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García JM, Maestro MA, Oiarbide M, et al. Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation. Org Lett. 2009;11(17):3826-9doi: 10.1021/ol901351k.
García, J. M., Maestro, M. A., Oiarbide, M., Odriozola, J. M., Razkin, J., & Palomo, C. (2009). Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation. Organic letters, 11(17), 3826-9. https://doi.org/10.1021/ol901351k
García, Jesús M, et al. "Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation." Organic letters vol. 11,17 (2009): 3826-9. doi: https://doi.org/10.1021/ol901351k
García JM, Maestro MA, Oiarbide M, Odriozola JM, Razkin J, Palomo C. Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation. Org Lett. 2009 Sep 03;11(17):3826-9. doi: 10.1021/ol901351k. PMID: 19663464.
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Org Lett. 2009 Sep 03;11(17):3826-9. doi: 10.1021/ol901351k.

Conjugate addition of nitroalkanes to an acrylate equivalent. Stereocontrol at C-alpha of the nitro group through double catalytic activation.

Organic letters

Jesús M García, Miguel A Maestro, Mikel Oiarbide, José M Odriozola, Jesús Razkin, Claudio Palomo

Affiliations

  1. Departamento de Química Aplicada, Universidad Pública de Navarra, Pamplona, Spain.

PMID: 19663464 DOI: 10.1021/ol901351k

Abstract

An unprecedented highly selective direct conjugate addition of prochiral nitroalkanes (R not equal H) to acrylate equivalents is described. The method employs a unique Lewis acid/Brønsted base/MS ternary catalytic system and affords products with dr up to 97/3. With beta-substituted (R' not equal H) acceptors unprecedented levels of anti/syn selectivity (>or=96/4) are attained. Adducts can be transformed into enantioenriched gamma-amino acids and derivatives, including aldehydes, ketones, lactams, and peptides, through simple protocols with full recovery of camphor auxiliary, the source of chiral information.

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