PMID: 11925246Apr 2, 2002Paper

Chiral tricyclic iminolactone derived from (1R)-(+)-camphor as a glycine equivalent for the asymmetric synthesis of alpha-amino acids

The Journal of Organic Chemistry
Peng-Fei XuTa-Jung Lu

Abstract

The development of a highly efficient and stereoselective methodology for the preparation of alpha-amino acids is described. The chiral template, tricyclic iminolactone 7, was synthesized from (1R)-(+)-camphor in five steps in 50% overall yield. Alkylation of iminolactone 7 afforded the alpha-monosubstituted products in good yields (74-96%) and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired alpha-amino acids in good yields and enantioselectivities with nearly quantitative recovery of the chiral auxiliary 4.

Citations

Feb 22, 2012·Acta Crystallographica. Section E, Structure Reports Online·Jason A JordonJames A Golen
Jul 21, 2016·Organic Letters·Xiaoyu LanBaoguo Zhao
Sep 21, 2005·Organic & Biomolecular Chemistry·Jasper KaiserFloris P J T Rutjes
Jan 26, 2007·Organic & Biomolecular Chemistry·Henning Vogt, Stefan Bräse
Jan 13, 2012·Organic & Biomolecular Chemistry·Ramalingam BoobalanGene-Hsian Lee
Mar 25, 2010·The Journal of Organic Chemistry·Feng-Feng GanPeng-Fei Xu
May 8, 2015·Journal of Natural Products·Xuemei LiuSøren Brøgger Christensen
Aug 3, 2010·Accounts of Chemical Research·Yong-Chun LuoPeng-Fei Xu

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