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Journal articles on the topic 'Carbenoid use in synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Cuevas-Yañez, Erick, Juan Manuel Serrano, Gloria Huerta, Joseph M. Muchowski, and Raymundo Cruz-Almanza. "Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole." Tetrahedron 60, no. 42 (October 2004): 9391–96. http://dx.doi.org/10.1016/j.tet.2004.08.009.

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2

SATOH, Tsuyoshi. "Exploitation of the Chemistry of Magnesium Carbenoids and Their Use in Organic Synthesis." YAKUGAKU ZASSHI 129, no. 9 (September 1, 2009): 1013–23. http://dx.doi.org/10.1248/yakushi.129.1013.

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3

Haigh, David. "Rhodium carbenoid O-H insertion reactions with phenols; A facile method for the synthesis of trialkyl 2-aryloxyphosphonoacetates and their use in the preparation of 2-aryloxy-3-phenylpropanoates." Tetrahedron 50, no. 10 (March 1994): 3177–94. http://dx.doi.org/10.1016/s0040-4020(01)81116-9.

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4

HAIGH, D. "ChemInform Abstract: Rhodium Carbenoid O-H Insertion Reactions with Phenols; a Facile Method for the Synthesis of Trialkyl 2-Aryloxyphosphonoacetates and Their Use in the Preparation of 2-Aryloxy-3-phenylpropanoates." ChemInform 25, no. 29 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199429076.

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5

Matsumoto, Kozo, Yoshitaka Aoki, Koichiro Oshima, Kiitiro Utimoto, and Noorsaadah Abd Rahman. "Lithium carbenoids induced ring enlargement of silacyclobutane into 2-halo-1-silacyclopentane and its use in organic synthesis." Tetrahedron 49, no. 38 (September 1993): 8487–502. http://dx.doi.org/10.1016/s0040-4020(01)96257-x.

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6

MATSUMOTO, K., Y. AOKI, K. OSHIMA, K. UTIMOTO, and N. A. RAHMAN. "ChemInform Abstract: Lithium Carbenoids Induced Ring Enlargement of Silacyclobutane into 2- Halo-1-silacyclopentane and Its Use in Organic Synthesis." ChemInform 25, no. 2 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199402208.

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7

Ma, Xiaochu, Stefan M. Cooper, Fan Yang, Wenhao Hu, and Herman O. Sintim. "Alkaloid Synthesis via Carbenoid Intermediates." Current Organic Chemistry 20, no. 1 (October 26, 2015): 82–101. http://dx.doi.org/10.2174/1385272819666150810225759.

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8

Buck, Richard T., Paul A. Clarke, Diane M. Coe, Martin J. Drysdale, Leigh Ferris, David Haigh, Christopher J. Moody, Neil D. Pearson, and Elizabeth Swann. "The Carbenoid Approach to Peptide Synthesis." Chemistry - A European Journal 6, no. 12 (June 16, 2000): 2160–67. http://dx.doi.org/10.1002/1521-3765(20000616)6:12<2160::aid-chem2160>3.0.co;2-y.

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9

Chalifoux, Wesley A., and Rik R. Tykwinski. "Polyyne synthesis using carbene/carbenoid rearrangements." Chemical Record 6, no. 4 (2006): 169–82. http://dx.doi.org/10.1002/tcr.20081.

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10

Tezuka, Yasuyuki, Yasufumi Nakayama, Koh Ushizaka, and Kiyokazu Imai. "Carbenoid polycondensation. 2. Synthesis of unsaturated polyesters through the polycondensation of carbenoid intermediates." Macromolecules 26, no. 5 (September 1993): 921–25. http://dx.doi.org/10.1021/ma00057a007.

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11

ITOH, Katsuji, Tsutomu FUKUDA, Hiroshi KITAJIMA, and Tsutomu KATSUKI. "New Aspect of Carbenoid Reaction: Exploitation of New Asymmetric Synthesis Using Chiral Carbenoid Species." Journal of Synthetic Organic Chemistry, Japan 55, no. 9 (1997): 764–73. http://dx.doi.org/10.5059/yukigoseikyokaishi.55.764.

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12

Marek, Ilan. "Sp3 organozinc carbenoid homologation in organic synthesis." Tetrahedron 58, no. 47 (November 2002): 9463–75. http://dx.doi.org/10.1016/s0040-4020(02)01186-9.

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13

Müller, Paul, and Philippe Polleux. "Synthesis of a Ketorolac ModelviaAromatic Carbenoid Insertion." Helvetica Chimica Acta 81, no. 2 (February 4, 1998): 317–23. http://dx.doi.org/10.1002/hlca.19980810212.

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14

Vaitla, Janakiram, Annette Bayer, and Kathrin H. Hopmann. "Vinyl Sulfoxonium Ylide: A New Vinyl Carbenoid Transfer Reagent for the Synthesis of Heterocycles." Synlett 30, no. 12 (April 10, 2019): 1377–83. http://dx.doi.org/10.1055/s-0037-1611771.

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Sulfoxonium ylides have recently gained prominence as safe carbenoid precursors in metal-catalyzed reactions. The stability and reactivity of sulfoxonium ylides depend on the substitution of the ylide carbon. The reactivity of vinyl-substituted sulfoxonium ylides is different and offers several advantages over known stabilized sulfoxonium ylides in the case of carbenoid transfer reactions. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of sulfoxonium ylide-derived vinyl carbenoid transformations for N-Heterocycles.1 Introduction2 Classification of Sulfoxonium Ylides3 Synthesis of Vinyl Sulfoxonium Ylides4 [3+2] Annulation of Vinyl Sulfoxonium Ylides5 [4+1] Annulation of Vinyl Sulfoxonium Ylides6 Conclusion

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15

Ferreira, Vitor. "Synthesis of Heterocyclic Compounds by Carbenoid Transfer Reactions." Current Organic Chemistry 11, no. 2 (January 1, 2007): 177–93. http://dx.doi.org/10.2174/138527207779316462.

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16

Heslin, Julie C., Christopher J. Moody, Alexandra M.Z. Slawin, and David J. Williams. "Synthesis of cyclic ethers by rhodium carbenoid cyclisation." Tetrahedron Letters 27, no. 12 (January 1986): 1403–6. http://dx.doi.org/10.1016/s0040-4039(00)84270-7.

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17

Gingras, Marc, and Fabien Dubois. "Synthesis of carbohelicenes and derivatives by “carbenoid couplings”." Tetrahedron Letters 40, no. 7 (February 1999): 1309–12. http://dx.doi.org/10.1016/s0040-4039(98)02670-7.

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18

Padwa, Albert, and Keith E. Krumpe. "Application of Intramolecular Carbenoid Reactions in Organic Synthesis." Tetrahedron 48, no. 26 (January 1992): 5385–453. http://dx.doi.org/10.1016/s0040-4020(01)88298-3.

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19

ITOH, K., T. FUKUDA, H. KITAJIMA, and T. KATSUKI. "ChemInform Abstract: New Aspect of Carbenoid Reaction: Exploitation of New Asymmetric Synthesis Using Chiral Carbenoid Species." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807279.

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20

Vaitla, Janakiram, and Annette Bayer. "Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis." Synthesis 51, no. 03 (December 12, 2018): 612–28. http://dx.doi.org/10.1055/s-0037-1610328.

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As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.1 Introduction2 Preparation of Sulfoxonium Ylides3 Investigation for Carbenoid Formation from Sulfoxonium Ylide 4 X–H (X = N, O, S, C) Functionalization Reactions5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides6 Conclusion and Perspective

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21

White, James D., Peter Hrnciar, and Frank Stappenbeck. "Asymmetric Total Synthesis of (+)-Codeine via Intramolecular Carbenoid Insertion." Journal of Organic Chemistry 64, no. 21 (October 1999): 7871–84. http://dx.doi.org/10.1021/jo990905z.

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22

Guo, Wengang, Min Wang, Zhengyu Han, Hai Huang, and Jianwei Sun. "Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides." Chemical Science 12, no. 33 (2021): 11191–96. http://dx.doi.org/10.1039/d1sc02439f.

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An organocatalytic asymmetric N–H insertion reaction of α-carbonyl sulfoxonium ylides has been developed to provide efficient access to α-amino esters without involving a metal carbenoid intermediate.

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23

Solé, Daniel, Ferran Pérez-Janer, and Israel Fernández. "Palladium-catalysed intramolecular carbenoid insertion of α-diazo-α-(methoxycarbonyl)acetanilides for oxindole synthesis." Chemical Communications 53, no. 21 (2017): 3110–13. http://dx.doi.org/10.1039/c7cc00718c.

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24

Ma, Xueji, Xuemei Xie, Li Liu, Ran Xia, Tongyu Li, and Hangxiang Wang. "Facile synthesis of pyrroloindoles via a rhodium(ii)-catalyzed annulation of 3-benzylidene-indolin-2-ones and α-imino carbenes." Chemical Communications 54, no. 13 (2018): 1595–98. http://dx.doi.org/10.1039/c7cc08438b.

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25

Allouche, Emmanuelle M. D., Sylvain Taillemaud, and André B. Charette. "Spectroscopic characterization of (diiodomethyl)zinc iodide: application to the stereoselective synthesis and functionalization of iodocyclopropanes." Chemical Communications 53, no. 69 (2017): 9606–9. http://dx.doi.org/10.1039/c7cc04348a.

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26

Ma, Xueji, Feifei Wu, Xiaofei Yi, Hangxiang Wang, and Wanzhi Chen. "One-pot synthesis of 2,3-disubstituted dihydrobenzofurans and benzofurans via rhodium-catalyzed intramolecular C–H insertion reaction." Chemical Communications 51, no. 31 (2015): 6862–65. http://dx.doi.org/10.1039/c5cc01271f.

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27

Franceschi, Giovanni, Pierluigi Bissolino, Marco Alpegiani, Daniela Borghi, and Ettore Perrone. "Synthesis of Penams from 1H-Azetidinones by Intramolecular Carbenoid Insertion." HETEROCYCLES 36, no. 7 (1993): 1529. http://dx.doi.org/10.3987/com-92-6326.

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28

Kasatkin, Alexander N., and Richard J. Whitby. "Carbenoid insertion into alkenylzirconocenes—a convergent synthesis of functionalised allylmetallics." Tetrahedron Letters 41, no. 32 (August 2000): 6211–16. http://dx.doi.org/10.1016/s0040-4039(00)01024-8.

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29

Moody, Christopher J., Christopher J. Pearson, and Geoffrey Lawton. "Synthesis of aza-β-lactams by rhodium carbenoid mediated cyclisation." Tetrahedron Letters 26, no. 26 (January 1985): 3171–72. http://dx.doi.org/10.1016/s0040-4039(00)98648-9.

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30

Heslin, Julie C., and Christopher J. Moody. "Rhodium carbenoid mediated cyclisations. Part 2. Synthesis of cyclic ethers." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1417. http://dx.doi.org/10.1039/p19880001417.

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31

Shi Shun, Annabelle L. K., and Rik R. Tykwinski. "Synthesis of Naturally Occurring Acetylenes via an Alkylidene Carbenoid Rearrangement." Journal of Organic Chemistry 68, no. 17 (August 2003): 6810–13. http://dx.doi.org/10.1021/jo034734g.

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32

PADWA, A., and K. E. KRUMPE. "ChemInform Abstract: Application of Intramolecular Carbenoid Reactions in Organic Synthesis." ChemInform 23, no. 42 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199242262.

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33

Lv, Honggui, Jingjing Shi, Bo Wu, Yujuan Guo, Junjun Huang, and Wei Yi. "One-pot synthesis of 2,3-difunctionalized indoles via Rh(iii)-catalyzed carbenoid insertion C–H activation/cyclization." Organic & Biomolecular Chemistry 15, no. 38 (2017): 8054–58. http://dx.doi.org/10.1039/c7ob01977g.

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34

Shi, Jingjing, Jie Zhou, Yunnan Yan, Jinlong Jia, Xuelei Liu, Huacan Song, H. Eric Xu, and Wei Yi. "One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(iii)-catalyzed carbenoid insertion C–H activation/cyclization." Chemical Communications 51, no. 4 (2015): 668–71. http://dx.doi.org/10.1039/c4cc08407a.

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35

Silva, Pedro J., and Carlos E. P. Bernardo. "Unveiling the Reaction Mechanism of the Das/Chechik/Marek Synthesis of Stereodefined Quaternary Carbon Centers." Applied Sciences 11, no. 11 (May 28, 2021): 5002. http://dx.doi.org/10.3390/app11115002.

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The reaction mechanism of the Cu+-catalyzed introduction of two all-carbon-substituted stereocenters in an ynamide system using a Grignard reagent, a zinc carbenoid, and an aldehyde, was investigated using density-functional theory. In contrast to the formation of an organocopper(I) compound and subsequent carbocupration reaction, previously postulated as the initial step, the reaction proved to instead proceed through an initial complexation of the substrate alkyne bond by the Cu+-catalyst, which primes this bond for reaction with the Grignard reagent. Subsequent addition of the zinc carbenoid then enables the nucleophilic attack on the incoming aldehyde, which is revealed as the rate-limiting step. Our computations have also identified the factors governing the regio- and setereoselectivity of this interesting reaction, and suggest possible paths for its further development.

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36

Rudolph, Matthias, Melissa Q. McCreery, Wolfgang Frey, and A. Stephen K. Hashmi. "High chemoselectivity in the phenol synthesis." Beilstein Journal of Organic Chemistry 7 (June 10, 2011): 794–801. http://dx.doi.org/10.3762/bjoc.7.90.

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Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of the gold-catalyzed phenol synthesis are much faster than the steps of the interception reaction. In the latter the barrier of activation is higher. At the same time this explains the high tolerance of this very efficient and general reaction towards functional groups.

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37

Hayes, Theodore O. P., Ben Slater, Richard A. J. Horan, Marc Radigois, and Jonathan D. Wilden. "A novel sulfonamide non-classical carbenoid: a mechanistic study for the synthesis of enediynes." Organic & Biomolecular Chemistry 15, no. 46 (2017): 9895–902. http://dx.doi.org/10.1039/c7ob02437a.

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Alkynyl sulfonamides undergo sequential 1,4- then 1,2-addition/rearrangement with lithium acetylides to yield enediynes in the absence of any promoters or catalysts. Mechanistic investigations suggest that the reaction proceeds via a novel electrophilic carbenoid with distinct reactivity compared to those previously described.

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38

Moody, Christopher J., and Roger J. Taylor. "Rhodium carbenoid mediated cyclisations. Synthesis and rearrangement of cyclic sulphonium ylides." Tetrahedron Letters 29, no. 46 (January 1988): 6005–8. http://dx.doi.org/10.1016/s0040-4039(00)82252-2.

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39

Aburel, Pompiliu S., and Kjell Undheim. "Synthesis of spirosystems by rhodium(II)-carbenoid CH insertion reactions." Tetrahedron Letters 39, no. 22 (May 1998): 3813–14. http://dx.doi.org/10.1016/s0040-4039(98)00591-7.

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40

Stow, Caroline P., and Ross A. Widenhoefer. "Synthesis, Structure, and Reactivity of Gold(I) α-Oxo Carbenoid Complexes." Organometallics 39, no. 8 (March 24, 2020): 1249–57. http://dx.doi.org/10.1021/acs.organomet.0c00033.

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41

Moody, Christopher J., and Roger J. Taylor. "Rhodium carbenoid mediated cyclisations. Part 6. Synthesis of cyclic sulphoxonium ylides." Tetrahedron 46, no. 18 (January 1990): 6525–44. http://dx.doi.org/10.1016/s0040-4020(01)96018-1.

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42

Kim, Guncheol, Sunwha Kang, and Gyochang Keum. "A synthesis of (±)-supinidine via an intramolecular carbenoid-thioimide coupling reaction." Tetrahedron Letters 35, no. 22 (May 1994): 3747–48. http://dx.doi.org/10.1016/s0040-4039(00)73088-7.

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43

Na, Sung Jae, Bun Yeoul Lee, Nhat-Nguyen Bui, Sun-il Mho, and Hye-Young Jang. "A new dirhodium tetraacetate carbenoid: Synthesis, crystal structure and catalytic application." Journal of Organometallic Chemistry 692, no. 24 (November 2007): 5523–27. http://dx.doi.org/10.1016/j.jorganchem.2007.09.004.

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44

Loy, Nicole S. Y., Alok Singh, Xianxiu Xu, and Cheol-Min Park. "Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines." Angewandte Chemie International Edition 52, no. 8 (January 10, 2013): 2212–16. http://dx.doi.org/10.1002/anie.201209301.

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45

Hansen, Karl B., Nathaniel S. Finney, and Eric N. Jacobsen. "Carbenoid Transfer to Imines: A New Asymmetric Catalytic Synthesis of Aziridines." Angewandte Chemie International Edition in English 34, no. 6 (March 31, 1995): 676–78. http://dx.doi.org/10.1002/anie.199506761.

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46

White, James D., Peter Hrnciar, and Frank Stappenbeck. "ChemInform Abstract: Asymmetric Total Synthesis of (+)-Codeine via Intramolecular Carbenoid Insertion." ChemInform 31, no. 5 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200005247.

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47

MUELLER, P., and P. POLLEUX. "ChemInform Abstract: Synthesis of a Ketorolac Model via Aromatic Carbenoid Insertion." ChemInform 29, no. 20 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199820139.

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48

Jefford, Charles W., Tadatoshi Kubota, and Alexander Zaslona. "Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine." Helvetica Chimica Acta 69, no. 8 (December 10, 1986): 2048–61. http://dx.doi.org/10.1002/hlca.19860690828.

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49

Loy, Nicole S. Y., Alok Singh, Xianxiu Xu, and Cheol-Min Park. "Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines." Angewandte Chemie 125, no. 8 (January 10, 2013): 2268–72. http://dx.doi.org/10.1002/ange.201209301.

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50

Davis, Franklin A., Bin Yang, and Jianghe Deng. "Asymmetric Synthesis ofcis-5-tert-Butylproline with Metal Carbenoid NH Insertion." Journal of Organic Chemistry 68, no. 13 (June 2003): 5147–52. http://dx.doi.org/10.1021/jo030081s.

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