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Journal articles on the topic 'Felkin-Anh'

Author: Grafiati
Published: 4 June 2021
Last updated: 8 February 2022

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1

Rosenberg, Robert E., and W. Jonathan Kelly. "Felkin-Anh is not enough." Journal of Physical Organic Chemistry 28, no. 1 (November 27, 2014): 47–56. http://dx.doi.org/10.1002/poc.3397.

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2

Bailey, Constance B., Marjolein E. Pasman, and Adrian T. Keatinge-Clay. "Substrate structure–activity relationships guide rational engineering of modular polyketide synthase ketoreductases." Chemical Communications 52, no. 4 (2016): 792–95. http://dx.doi.org/10.1039/c5cc07315d.

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Structure–activity relationship studies guided stereocontrol engineering within a modular polyketide synthase ketoreductase to yield a more active enzyme whose reactivity can be explained through the Felkin–Anh model.
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3

Hein, S. J., and D. A. Keszler. "A product predicted with the Felkin–Anh model." Acta Crystallographica Section C Crystal Structure Communications 43, no. 12 (December 15, 1987): 2457–59. http://dx.doi.org/10.1107/s0108270187087365.

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4

Smith, Richard J., Michael Trzoss, Michael Bühl, and Stefan Bienz. "The Cram Rule Revisited Once More — Revision of the Felkin−Anh Model." European Journal of Organic Chemistry 2002, no. 16 (August 2002): 2770. http://dx.doi.org/10.1002/1099-0690(200208)2002:16<2770::aid-ejoc2770>3.0.co;2-x.

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5

Spino, Claude, Marie-Claude Granger, Luc Boisvert, and Christian Beaulieu. "Increased Felkin–Anh selectivity in nucleophilic additions to α-chiral aldehydes using vinylalanes." Tetrahedron Letters 43, no. 23 (June 2002): 4183–85. http://dx.doi.org/10.1016/s0040-4039(02)00753-0.

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6

Christoffers, Jens, Heiko Scharl, Wolfgang Frey, and Angelika Baro. "Transformation of an Optically Active Decahydro-6-isoquinolone Scaffold: Perfect Felkin−Anh Diastereoselectivity." Organic Letters 6, no. 7 (April 2004): 1171–73. http://dx.doi.org/10.1021/ol049831q.

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7

Shumway, William, Sihyun Ham, Jessica Moer, Bruce R. Whittlesey, and David M. Birney. "Felkin−Anh Stereoselectivity in Cycloadditions of Acetylketene: Evidence for a Concerted, Pseudopericyclic Pathway." Journal of Organic Chemistry 65, no. 23 (November 2000): 7731–39. http://dx.doi.org/10.1021/jo0002644.

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8

Myeong, In-Soo, Jin-Seok Kim, Muyng-Gyu Park, Hwan-Hee Jeon, Changyoung Jung, Yong-Taek Lee, and Won-Hun Ham. "Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines." Synthesis 50, no. 10 (March 27, 2018): 2058–66. http://dx.doi.org/10.1055/s-0037-1609343.

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The stereoselective allylations of β-amino-α-hydroxy aldehydes­ are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2­, and MgBr2·OEt2) were utilized in the allylations. The allylation of anti-β-NHCbz-α-OTBS substrate mediated by SnCl4 afforded the syn-selective­ product, while its allylation mediated by BF3·OEt2 afforded the anti-selective product. The allylation of syn-β-NHCbz-α-OTBS mediated by SnCl4 afforded the anti-selective product. The mechanism involves the chelation between the amido group and aldehyde oxygen by SnCl4, and the Felkin–Anh model by BF3·OEt2. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines.
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9

Bubert, Christian, and Oliver Reiser. "Exceptionally high Felkin-Anh control for the addition of nucleophiles to a β-aminocyclopropylcarbaldehyde." Tetrahedron Letters 38, no. 28 (July 1997): 4985–88. http://dx.doi.org/10.1016/s0040-4039(97)01065-4.

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10

Giese, Bernd, Wolfgang Damm, Martin Roth, and Margaretha Zehnder. "The Felkin-Anh Rule in Radical Chemistry: 1,2-Stereoinduction in Radical Addition to Alkenes." Synlett 1992, no. 05 (1992): 441–43. http://dx.doi.org/10.1055/s-1992-21374.

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11

Smadja, William, Mohamed Zahouily, and Max Malacria. "Stereoselective additions of silicon centered radical to α-chiral olefins: A Felkin-Anh stereoelectronic control." Tetrahedron Letters 33, no. 38 (September 1992): 5511–14. http://dx.doi.org/10.1016/s0040-4039(00)61131-0.

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12

Hashimoto, Toru, Jun-ichi Ito, and Hisao Nishiyama. "Felkin–Anh selectivity in Rh(bisoxazolinylphenyl)-catalyzed reductive aldol coupling reaction: asymmetric synthesis of stereotriads." Tetrahedron 64, no. 40 (September 2008): 9408–12. http://dx.doi.org/10.1016/j.tet.2008.07.092.

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13

Spino, Claude, Marie-Claude Granger, Luc Boisvert, and Christian Beaulieu. "ChemInform Abstract: Increased Felkin-Anh Selectivity in Nucleophilic Additions to α-Chiral Aldehydes Using Vinylalanes." ChemInform 33, no. 38 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200238035.

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14

Yang, Xing, Peng Liu, K. N. Houk, and Vladimir B. Birman. "Manifestation of Felkin-Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids." Angewandte Chemie 124, no. 38 (August 22, 2012): 9776–80. http://dx.doi.org/10.1002/ange.201203327.

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15

Yang, Xing, Peng Liu, K. N. Houk, and Vladimir B. Birman. "Manifestation of Felkin-Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids." Angewandte Chemie International Edition 51, no. 38 (August 22, 2012): 9638–42. http://dx.doi.org/10.1002/anie.201203327.

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16

Fleming, Ian, David A. Hrovat, and Weston Thatcher Borden. "The origin of Felkin–Anh control from an electropositive substituent adjacent to the carbonyl group †." Journal of the Chemical Society, Perkin Transactions 2, no. 3 (2001): 331–38. http://dx.doi.org/10.1039/b008409n.

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17

Giese, Bernd, Bertrand Carboni, Thomas Göbel, Ralf Muhn, and Frank Wetterich. "A new route to 3-deoxy-d-manno2-octulosonic acid: felkin-anh rule in radical chemistry." Tetrahedron Letters 33, no. 19 (May 1992): 2673–76. http://dx.doi.org/10.1016/s0040-4039(00)79054-x.

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18

Mulzer, Johann, Thomas Schulze, Achim Strecker, and Wolfgang Denzer. "Felkin-Anh-selective Hiyama addition to O-protected lactaldehydes: a general solution to the blastmycinone stereoproblem." Journal of Organic Chemistry 53, no. 17 (August 1988): 4098–103. http://dx.doi.org/10.1021/jo00252a040.

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19

BUBERT, C., and O. REISER. "ChemInform Abstract: Exceptionally High Felkin-Anh Control for the Addition of Nucleophiles to a β-Aminocyclopropylcarbaldehyde." ChemInform 28, no. 42 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199742092.

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20

SMADJA, W., M. ZAHOUILY, and M. MALACRIA. "ChemInform Abstract: Stereoselective Additions of Silicon Centered Radical to α- Chiral Olefins: A Felkin-Anh Stereoelectronic Control." ChemInform 24, no. 5 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199305244.

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21

Kaneno, Daisuke, and Shuji Tomoda. "Origin of facial diastereoselection in 2-adamantyl cations. Theoretical evidence against the Felkin–Anh and the Cieplak models." Tetrahedron Letters 45, no. 23 (May 2004): 4559–62. http://dx.doi.org/10.1016/j.tetlet.2004.04.036.

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22

Damm, Wolfgang, Joachim Dickhaut, Frank Wetterich, and Bernd Giese. "Transition states for the hydrogen atom abstraction reaction by ga-oxygen substituted radicals: Felkin-Anh Rule in Radical Chemistry." Tetrahedron Letters 34, no. 3 (January 1993): 431–34. http://dx.doi.org/10.1016/0040-4039(93)85094-d.

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23

Spino, Claude, Marie-Claude Granger, and Marie-Claude Tremblay. "Increased Felkin−Anh Selectivity Using AlMe3in the Addition of Vinyllithiums to α-Chiral Aldehydes: Do “Ate” Complexes Play Any Role?" Organic Letters 4, no. 26 (December 2002): 4735–37. http://dx.doi.org/10.1021/ol027236n.

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24

Marco, J. Alberto, Miguel Carda, Santiago Díaz-Oltra, Juan Murga, Eva Falomir, and Harald Roeper. "Double Diastereoselection in Aldol Reactions Mediated by Dicyclohexylchloroborane betweenl-Erythrulose Derivatives and Chiral Aldehydes. The Felkin−Anh versus Cornforth Dichotomy." Journal of Organic Chemistry 68, no. 22 (October 2003): 8577–82. http://dx.doi.org/10.1021/jo035159j.

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25

Cee, Victor J., Christopher J. Cramer, and David A. Evans. "Theoretical Investigation of Enolborane Addition to α-Heteroatom-Substituted Aldehydes. Relevance of the Cornforth and Polar Felkin−Anh Models for Asymmetric Induction." Journal of the American Chemical Society 128, no. 9 (March 2006): 2920–30. http://dx.doi.org/10.1021/ja0555670.

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26

Díaz-Oltra, Santiago, Miguel Carda, Juan Murga, Eva Falomir, and J. Alberto Marco. "Aldol Reactions between L-Erythrulose Derivatives and Chiral α-Amino and α-Fluoro Aldehydes: Competition between Felkin-Anh and Cornforth Transition States." Chemistry - A European Journal 14, no. 30 (October 20, 2008): 9240–54. http://dx.doi.org/10.1002/chem.200800956.

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27

Mulzer, Johann, Lars Kattner, Achim R. Strecker, Christian Schroeder, Juergen Buschmann, Christian Lehmann, and Peter Luger. "Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer." Journal of the American Chemical Society 113, no. 11 (May 1991): 4218–29. http://dx.doi.org/10.1021/ja00011a025.

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28

MULZER, J., L. KATTNER, A. R. STRECKER, C. SCHROEDER, J. BUSCHMANN, C. LEHMANN, and P. LUGER. "ChemInform Abstract: Highly Felkin-Anh Selective Hiyama Additions of Chiral Allylic Bromides to Aldehydes. Application to the First Synthesis of Nephromopsinic Acid and Its Enantiomer." ChemInform 22, no. 37 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199137269.

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29

Bartolo, Nicole D., Jacquelyne A. Read, Elizabeth M. Valentín, and K. A. Woerpel. "Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models." Chemical Reviews 120, no. 3 (January 6, 2020): 1513–619. http://dx.doi.org/10.1021/acs.chemrev.9b00414.

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30

Kobunshi 46, no. 2 (1997): 77a. http://dx.doi.org/10.1295/kobunshi.46.77a.

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31

Christoffers, Jens, Heiko Scharl, Wolfgang Frey, and Angelika Baro. "Transformation of an Optically Active Decahydro-6-isoquinolone Scaffold: Perfect Felkin—Anh Diastereoselectivity." ChemInform 35, no. 33 (August 17, 2004). http://dx.doi.org/10.1002/chin.200433164.

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32

MULZER, J., T. SCHULZE, A. STRECKER, and W. DENZER. "ChemInform Abstract: Felkin-Anh-Selective Hiyama Addition to O-Protected Lactaldehydes: A General Solution of the Blastmycinone Stereoproblem." ChemInform 20, no. 5 (January 31, 1989). http://dx.doi.org/10.1002/chin.198905082.

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33

Diaz-Oltra, Santiago, Miguel Carda, Juan Murga, Eva Falomier, and J. Alberto Marco. "ChemInform Abstract: Aldol Reaction Between L-Erythrulose Derivatives and Chiral α-Amino and α-Fluoro Aldehydes: Competition Between Felkin-Anh and Cornforth Transition States." ChemInform 40, no. 2 (January 13, 2009). http://dx.doi.org/10.1002/chin.200902198.

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