Jump to main content
Jump to site search

Issue 15, 2005
Previous Article Next Article

Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (−)-kainic acid

Author affiliations

Abstract

A survey of 16 different chiral auxiliaries and a variety of strategies found that an (−)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)-HyMePro and (−)-kainic acid.

Graphical abstract: Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (−)-kainic acid

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 May 2005, accepted on 06 Jun 2005 and first published on 30 Jun 2005


Article type: Paper
DOI: 10.1039/B506198A
Citation: Org. Biomol. Chem., 2005,3, 2741-2749
  •   Request permissions

    Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (−)-kainic acid

    J. C. Anderson, J. M. A. O'Loughlin and J. A. Tornos, Org. Biomol. Chem., 2005, 3, 2741
    DOI: 10.1039/B506198A

Search articles by author

Spotlight

Advertisements