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Journal articles on the topic 'Intramolecular Michael addition'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Reddy, S. Madhava, and H. M. Walborsky. "A facile intramolecular Michael addition reaction." Journal of Organic Chemistry 51, no. 13 (1986): 2605–7. http://dx.doi.org/10.1021/jo00363a042.

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2

You, S. L., Q. Cai, and C. Zheng. "Intramolecular Aza-Michael Addition of Indoles." Synfacts 2010, no. 12 (2010): 1428. http://dx.doi.org/10.1055/s-0030-1258922.

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3

Sánchez-Roselló, María, Carlos del Pozo, and Javier Miró. "Cross-Metathesis/Intramolecular (Hetero-)Michael Addition: A Convenient Sequence for the Generation of Carbo- and Heterocycles." Synthesis 49, no. 13 (2017): 2787–802. http://dx.doi.org/10.1055/s-0036-1589497.

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The high stability and functional group compatibility of ruthenium carbene complexes confer them a great ability to catalyze domino processes. For this reason, the combination of metathesis reactions with additional transformations in a domino fashion has been exploited extensively, with the result of expanding the utility of ruthenium carbene complexes beyond that of just olefin metathesis. Among those domino processes, it is worth mentioning the sequence of cross-metathesis/intramolecular Michael addition, which allows for the generation of a wide variety of carbo- and heterocycles in a very

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4

Ellis, Graham W. L., C. David Johnson, and David N. Rogers. "Electronic Effects in Intramolecular Michael Addition Reactions." Bulletin des Sociétés Chimiques Belges 91, no. 5 (2010): 437. http://dx.doi.org/10.1002/bscb.19820910596.

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5

Bates, Roderick W., Weiting Ko, and Viktor Barát. "The endo-aza-Michael addition in the synthesis of piperidines and pyrrolidines." Organic & Biomolecular Chemistry 18, no. 5 (2020): 810–29. http://dx.doi.org/10.1039/c9ob02388g.

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6

Lee, Jusung, Kwang Min Ko, and Sung-Gon Kim. "Asymmetric synthesis of 2,3-disubstituted indolines via an organocatalytic intramolecular Michael addition." RSC Advances 7, no. 89 (2017): 56457–62. http://dx.doi.org/10.1039/c7ra10775g.

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7

Bhusainahalli, Vedamurthy M., Antonio Rescifina, Nunzio Cardullo, Carmela Spatafora, and Corrado Tringali. "Bio-activated intramolecular anti-aza-Michael addition: stereoselective synthesis of hydantoin derivatives." New Journal of Chemistry 42, no. 22 (2018): 18348–57. http://dx.doi.org/10.1039/c8nj02909a.

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8

Goud, B. Satish, Kaliyamoorthy Panneerselvam, David E. Zacharias, and Gautam R. Desirajua. "Intramolecular Michael-type addition in the solid state." Journal of the Chemical Society, Perkin Transactions 2, no. 2 (1995): 325. http://dx.doi.org/10.1039/p29950000325.

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9

Liang, F., Y. Li, X. Bi, and Q. Liu. "Substituted Thiophenes via Intramolecular Thia-anti-Michael Addition." Synfacts 2007, no. 1 (2007): 0031. http://dx.doi.org/10.1055/s-2006-955741.

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10

Guo, Jiajia, and Shouyun Yu. "Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation." Organic & Biomolecular Chemistry 13, no. 4 (2015): 1179–86. http://dx.doi.org/10.1039/c4ob02227k.

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11

Girard, Suzanne, and Pierre Deslongchamps. "Formation of 14-membered carbocycles by intramolecular Michael addition on ynones and enones." Canadian Journal of Chemistry 70, no. 5 (1992): 1265–73. http://dx.doi.org/10.1139/v92-163.

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12

Shu, Tao, Sun Li, Xiang-Yu Chen, et al. "Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition." Chemical Communications 54, no. 55 (2018): 7661–64. http://dx.doi.org/10.1039/c8cc04145h.

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The first example of an N-heterocyclic carbene-catalyzed asymmetric desymmetrization of enal-tethered cyclohexadienones via an intramolecular homoenolate Michael addition/esterification reaction is described.

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13

Bayly, C. I., and F. Grein. "Comparison of an intramolecular Michael-type addition with its intermolecular counterpart: an abinitio theoretical study." Canadian Journal of Chemistry 67, no. 12 (1989): 2173–77. http://dx.doi.org/10.1139/v89-337.

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Abinitio theoretical calculations were carried out on the intramolecular addition of 3-ketopent-4-en-1-olate 1 to form 1-oxacyclohex-3-en-4-olate 2 (reaction I; Scheme 1) and the corresponding intermolecular Michael addition of methanolate to butenone forming 4-methoxybut-2-en-2-olate 4 (reaction II; Scheme 1). The calculations were carried out at the RHF level using an augmented 4-31G basis set; single point energies were then taken using the 6-31 + G* basis set. The overall energy change of the reaction in going from reactants to products is very similar for both reactions, with products bei

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14

Guevara-Pulido, James O., José M. Andrés, Deisy P. Ávila, and Rafael Pedrosa. "Enantioselective synthesis of seven-membered carbo- and heterocyles by organocatalyzed intramolecular Michael addition." RSC Advances 6, no. 36 (2016): 30166–69. http://dx.doi.org/10.1039/c6ra04198a.

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15

Ruel, Réjean, та Pierre Deslongchamps. "Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds". Canadian Journal of Chemistry 68, № 11 (1990): 1917–22. http://dx.doi.org/10.1139/v90-296.

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The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

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16

Chang, Meng-Yang, and Kuan-Ting Chen. "Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans." RSC Advances 13, no. 43 (2023): 29894–903. http://dx.doi.org/10.1039/d3ra06370d.

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The one-pot construction of diversified sulfonyl 2-aryl-5-methylenetetrahydropyrans is developed by DABCO-promoted intramolecular Michael addition of β-sulfonyl styrene with 2-chloromethyl-1-propenol followed by intramolecular alkylation.

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17

Stepanova, Ekaterina, Andrey Maslivets, Svetlana Kasatkina, and Maksim Dmitriev. "Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones." Synthesis 50, no. 24 (2018): 4897–904. http://dx.doi.org/10.1055/s-0037-1610647.

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A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intra

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18

Le Guen, Clothilde, Minh-Loan Tran Do, Aurélien Chardon, et al. "Access to Fluoropyrrolidines by Intramolecular Aza-Michael Addition Reaction." Journal of Organic Chemistry 81, no. 15 (2016): 6714–20. http://dx.doi.org/10.1021/acs.joc.6b01363.

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19

He, Hu, Li-Xin Dai, and Shu-Li You. "Intramolecular Michael addition reaction for the synthesis of benzylbutyrolactones." Organic & Biomolecular Chemistry 8, no. 14 (2010): 3207. http://dx.doi.org/10.1039/b924770j.

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20

Cheng, Shuanghua, and Shouyun Yu. "Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition." Org. Biomol. Chem. 12, no. 43 (2014): 8607–10. http://dx.doi.org/10.1039/c4ob01646g.

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A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er).

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21

Yan, Kelu, Min Liu, Jiangwei Wen, et al. "Synthesis of 3-substituted quinolines by ruthenium-catalyzed aza-Michael addition and intramolecular annulation of enaminones with anthranils." New Journal of Chemistry 46, no. 16 (2022): 7329–33. http://dx.doi.org/10.1039/d2nj00663d.

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22

Min, Junxiang, Guangyang Xu, and Jiangtao Sun. "A controlled selective synthesis of dihydropyrans through tandem reaction of alkynes with diazo compounds." Chemical Communications 53, no. 31 (2017): 4350–53. http://dx.doi.org/10.1039/c7cc01616f.

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23

Xiao, Ya-Ping, Xin-Yuan Liu та Chi-Ming Che. "Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones". Beilstein Journal of Organic Chemistry 7 (11 серпня 2011): 1100–1107. http://dx.doi.org/10.3762/bjoc.7.126.

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The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction conditions and the substrate scope of this reaction are examined, and a possible mechanism involving AgClO4 catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed.

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24

Karkhelikar, Manjusha V., Rajeev R. Jha, B. Sridhar, Pravin R. Likhar, and Akhilesh K. Verma. "An expedient approach to pyrrolo[3,2-c]quinolines via regioselective formation of the pyrrole nucleus over indoles." Chem. Commun. 50, no. 62 (2014): 8526–28. http://dx.doi.org/10.1039/c4cc02466d.

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25

Matsumoto, Akira, Keisuke Asano, and Seijiro Matsubara. "A chiral phosphoric acid catalyst for asymmetric construction of 1,3-dioxanes." Chemical Communications 51, no. 58 (2015): 11693–96. http://dx.doi.org/10.1039/c5cc04124d.

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26

Barrios Antúnez, Diego-Javier, Mark D. Greenhalgh, Charlene Fallan, Alexandra M. Z. Slawin, and Andrew D. Smith. "Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst." Organic & Biomolecular Chemistry 14, no. 30 (2016): 7268–74. http://dx.doi.org/10.1039/c6ob01326k.

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The enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives via intramolecular Michael addition has been developed using a bifunctional tertiary amine–thiourea catalyst.

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27

Deslongchamps, Pierre, and Bernard L. Roy. "Synthesis of 9- and 10-membered rings by the intramolecular Michael addition of malonate on enone and ynone." Canadian Journal of Chemistry 64, no. 10 (1986): 2068–75. http://dx.doi.org/10.1139/v86-342.

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The base-catalyzed (Cs2CO3 in THF/DMF) intramolecular Michael addition of β-ketoester-ynones 7–10 and -enone 11 is reported. Macrocyclization (Table 1), which produces the corresponding medium rings, was observed in 25–50% yield.

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28

Qiu, Lin, Xin Guo, Chaoqun Ma, et al. "Efficient synthesis of chiral cyclic acetals by metal and Brønsted acid co-catalyzed enantioselective four-component cascade reactions." Chem. Commun. 50, no. 17 (2014): 2196–98. http://dx.doi.org/10.1039/c3cc49063g.

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Four-component Mannich reactions subsequently followed by an intramolecular oxo-Michael addition were developed to efficiently produce chiral cyclic acetals with high diastereoselectivity and enantioselectivity.

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29

Murata, Ryuichi, Keisuke Asano, and Seijiro Matsubara. "Catalytic asymmetric cycloetherification via intramolecular oxy-Michael addition of enols." Tetrahedron 97 (September 2021): 132381. http://dx.doi.org/10.1016/j.tet.2021.132381.

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30

Rosenberg, Saul H., and Henry Rapoport. "Intramolecular Michael reactions. Addition to the .alpha.-carbon of ynamides." Journal of Organic Chemistry 50, no. 21 (1985): 3979–82. http://dx.doi.org/10.1021/jo00221a005.

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31

Bates, Roderick, and Tee Lek. "A Synthesis of Cyanolide A by Intramolecular Oxa-Michael Addition." Synthesis 46, no. 13 (2014): 1731–38. http://dx.doi.org/10.1055/s-0033-1341153.

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32

Sudhakar, Neela, Gannoju Srinivasulu, Ganipisetti Srinivas Rao, and Batchu Venkateswara Rao. "The formal synthesis of isofebrifugine using stereoselective intramolecular Michael addition." Tetrahedron: Asymmetry 19, no. 18 (2008): 2153–58. http://dx.doi.org/10.1016/j.tetasy.2008.08.021.

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33

Peng, Ying, Yongli Sun, Bo Wang, Yi Zhou, Shuangping Huang, and Xiaoji Wang. "Formal synthesis of (±)-aplykurodinone-1 through an intramolecular Michael addition." Tetrahedron Letters 60, no. 12 (2019): 839–42. http://dx.doi.org/10.1016/j.tetlet.2019.02.019.

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34

Ellis, Graham W. L., Donald F. Tavares, and Arvi Rauk. "The mechanism of an intramolecular Michael addition: a MNDO study." Canadian Journal of Chemistry 63, no. 12 (1985): 3510–15. http://dx.doi.org/10.1139/v85-575.

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The 5-endo-trig cyclization reactions of α′-hydroxy α,β-unsaturated carbonyl compounds to form the 3-furanone ring system has been investigated by means of MNDO calculations. In acid medium, the activation energy for ring formation is reduced by protonation of the carbonyl oxygen and by electron-releasing β-substituents, both of which facilitate torsion about the α,β-CC bond. Rotation about the α,β-CC bond is essentially complete when the transition structure is achieved. In reverse ring opening, heterolytic rupture of the C—O bond is aided by prior enolization since induced polarization of th

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35

Maezaki, Naoyoshi, Sachiko Yuyama, Hiroaki Sawamoto, Tomoko Suzuki, Mayuko Izumi та Tetsuaki Tanaka. "Highly Stereoselective Intramolecular Michael Addition Using α-Sulfinyl Vinyllithium as an Unprecedented Michael Donor". Organic Letters 3, № 1 (2001): 29–31. http://dx.doi.org/10.1021/ol006697a.

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36

Tong, Rongbiao, and Zhihong Zhang. "Synthetic Approaches to 2,6-trans-Tetrahydropyrans." Synthesis 49, no. 22 (2017): 4899–916. http://dx.doi.org/10.1055/s-0036-1588577.

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Being different from 2,6-cis-tetrahydropyrans (2,6-cis-THPs), the corresponding 2,6-trans-THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6-trans-THP subunit has led to the development of many efficient synthetic approaches to access 2,6-trans-THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products.1 Introduction2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A)3 Int

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37

Semakin, Artem N., Aleksandr O. Kokuev, Yulia V. Nelyubina, et al. "Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia." Beilstein Journal of Organic Chemistry 12 (November 21, 2016): 2471–77. http://dx.doi.org/10.3762/bjoc.12.241.

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Exhaustive Michael-type alkylations of amines and ammonia with azoalkenes (generated from α-halohydrazones) were demonstrated as an efficient approach to poly(hydrazonomethyl)amines – a novel class of polynitrogen ligands. An intramolecular cyclotrimerization of C=N bonds in tris(hydrazonomethyl)amine to the respective 1,4,6,10-tetraazaadamantane derivative was demonstrated.

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38

Lei, Chuan-Wen, Chuan-Bao Zhang, Zhen-Hua Wang, et al. "Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles." Organic & Biomolecular Chemistry 18, no. 5 (2020): 845–50. http://dx.doi.org/10.1039/c9ob02434d.

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39

Cui, L. Y., Y. H. Wang, S. R. Chen, Y. M. Wang, and Z. H. Zhou. "Stereocontrolled construction of 3H-furo[3,4-b]chromen-1(9H)-one scaffolds via organocatalyzed Michael addition and the following intramolecular dehydration." RSC Advances 5, no. 107 (2015): 88133–40. http://dx.doi.org/10.1039/c5ra17503h.

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Stereocontrolled construction of 3H-furo[3,4-b]chromen-1(9H)-one scaffolds has been realized via chiral squaramide catalyzed asymmetric Michael addition of tetronic acid to 2-((E)-2-nitrovinyl)phenols and the subsequent intramolecular dehydration.

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40

Nair, Deepa, Abhishek Tiwari, Banamali Laha, and Irishi N. N. Namboothiri. "Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates." Beilstein Journal of Organic Chemistry 20 (August 15, 2024): 2016–23. http://dx.doi.org/10.3762/bjoc.20.177.

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A cascade inter–intramolecular double Michael strategy for the synthesis of highly functionalized cyclohexanones from curcumins and arylidenemalonates is reported. This strategy works in the presence of aqueous KOH using TBAB as a suitable phase transfer catalyst at room temperature. The functionalized cyclohexanones are formed as major products in moderate to excellent yields with complete diastereoselectivity in most cases. A triple Michael adduct, tetrahydrochromen-4-one, is also formed as a side product in a few cases with excellent diastereoselectivity.

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41

Su, Guanglong, Connor J. Thomson, Ken Yamazaki та ін. "A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolines via intramolecular aza-Michael reaction to α,β-unsaturated esters". Chemical Science 12, № 17 (2021): 6064–72. http://dx.doi.org/10.1039/d1sc00856k.

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The activation of both aromatic and aliphatic ureas as N-centered nucleophiles in intramolecular Michael addition reactions to α,β-unsaturated esters was achieved under bifunctional iminophosphorane squaramide superbase catalysis.

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42

Vepreva, Anastasia, Alexander Yanovich, Dmitry Dar’in, Grigory Kantin, Alexander Bunev, and Mikhail Krasavin. "A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition." Beilstein Journal of Organic Chemistry 18 (December 6, 2022): 1649–55. http://dx.doi.org/10.3762/bjoc.18.177.

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A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh2(esp)2-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-trig oxa-Michael addition.

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43

Liu, Gang, Xuechun Sun, Ling Chen, et al. "Facile synthesis of quinoxaline annulated perfluoroalkylated benzoazepine derivatives." RSC Advances 6, no. 110 (2016): 108154–57. http://dx.doi.org/10.1039/c6ra22727a.

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Perfluoroalkylated benzoazepinoquinoxalines 3 were synthesized by a consecutive intermolecular Michael addition and intramolecular cyclization from 3-(2-aminophenyl)quinoxalin-2(1H)-ones 1 and methyl perfluoroalk-2-ynoates 2 in good yields.

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44

Fustero, Santos, Silvia Catalán, María Sánchez-Roselló, Antonio Simón-Fuentes, and Carlos del Pozo. "Tandem Asymmetric Michael Reaction−Intramolecular Michael Addition. An Easy Entry to Chiral Fluorinated 1,4-Dihydropyridines." Organic Letters 12, no. 15 (2010): 3484–87. http://dx.doi.org/10.1021/ol101318t.

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45

Harish, Battu, Sanjay Yadav, and Surisetti Suresh. "Design and application of intramolecular vinylogous Michael reaction for the construction of 2-alkenyl indoles." Chemical Communications 57, no. 2 (2021): 231–34. http://dx.doi.org/10.1039/d0cc06564a.

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A base mediated intramolecular vinylogous Michael addition has been disclosed for the first time for the construction of indoles and the synthesis of a wide range of 2-alkenyl indole derivatives in high yields.

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46

Cobb, A., W. Nodes, D. Nutt, and A. Chippindale. "Efficient Intramolecular Michael Addition of a Nitroalkane into a Conjugated Ester." Synfacts 2009, no. 12 (2009): 1399. http://dx.doi.org/10.1055/s-0029-1218211.

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47

Takasu, Kiyosei, Sayaka Mizutani, Miho Noguchi, Kei Makita, and Masataka Ihara. "Stereocontrolled Total Synthesis of (±)-Culmorin via the Intramolecular Double Michael Addition." Organic Letters 1, no. 3 (1999): 391–94. http://dx.doi.org/10.1021/ol9900562.

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48

Antonioletti, Roberto, Francesco Bonadies, Teresa Prencipe, and Arrigo Scettri. "Furan-3(2H)-ones by tandem photo-oxidation–intramolecular Michael addition." J. Chem. Soc., Chem. Commun., no. 13 (1988): 850–51. http://dx.doi.org/10.1039/c39880000850.

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49

Maezaki, Naoyoshi, Hiroaki Sawamoto, Sachiko Yuyama та ін. "Asymmetric Intramolecular Michael Addition of α-Sulfinyl Vinylic Carbanion to Enoates". Journal of Organic Chemistry 69, № 19 (2004): 6335–40. http://dx.doi.org/10.1021/jo0492923.

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50

Yuan, Haiyan, Yiying Zheng, and Jingping Zhang. "Mechanism Study of the Intramolecular Anti-Michael Addition of N-Alkylfurylacrylacetamides." Journal of Organic Chemistry 77, no. 19 (2012): 8744–49. http://dx.doi.org/10.1021/jo3018796.

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