Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids

Weiss M, Borchert S, Remond E, Juge S, Gröger H (2012)
Heteroatom Chemistry 23(2): 202-209.

Journal Article | Published | English

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Abstract
A proof of concept for the asymmetric organocatalytic aza-Michael addition reaction of nitrogen nucleophiles with simple and readily available alkyl enoates as acceptor molecules in the presence of a chiral phase-transfer catalyst has been demonstrated. The desired enantiomerically enriched beta-amino acid derivatives were obtained in up to 86% yield and with enantioselectivities of up to 37% ee. (C) 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:202209, 2012; View this article online at . DOI 10.1002/hc.21004
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Weiss M, Borchert S, Remond E, Juge S, Gröger H. Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids. Heteroatom Chemistry. 2012;23(2):202-209.
Weiss, M., Borchert, S., Remond, E., Juge, S., & Gröger, H. (2012). Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids. Heteroatom Chemistry, 23(2), 202-209.
Weiss, M., Borchert, S., Remond, E., Juge, S., and Gröger, H. (2012). Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids. Heteroatom Chemistry 23, 202-209.
Weiss, M., et al., 2012. Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids. Heteroatom Chemistry, 23(2), p 202-209.
M. Weiss, et al., “Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids”, Heteroatom Chemistry, vol. 23, 2012, pp. 202-209.
Weiss, M., Borchert, S., Remond, E., Juge, S., Gröger, H.: Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids. Heteroatom Chemistry. 23, 202-209 (2012).
Weiss, Markus, Borchert, Sonja, Remond, Emmanuelle, Juge, Sylvain, and Gröger, Harald. “Asymmetric addition of a nitrogen nucleophile to an enoate in the presence of a chiral phase-transfer catalyst: A novel approach toward enantiomerically enriched protected beta-amino acids”. Heteroatom Chemistry 23.2 (2012): 202-209.
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