Asymmetric synthesis of allylic secondary alcohols: a new general approach for the preparation of α-amino acids

Drummond, L.J. and Sutherland, A. (2010) Asymmetric synthesis of allylic secondary alcohols: a new general approach for the preparation of α-amino acids. Tetrahedron, 66(29), pp. 5349-5356. (doi: 10.1016/j.tet.2010.05.066)

Abstract

A new general approach for the synthesis of optically active α-amino acids has been developed. The key steps involve a ruthenium catalysed cross-coupling reaction to give a range of α,β-unsaturated ketones, which were then reduced to allylic secondary alcohols in the presence of a chiral CBS oxazaborolidine. A thermal Overman rearrangement was used to prepare a series of allylic trichloroacetimidates and these were converted under standard conditions to the target alpha-amino acids in good overall yields. .

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Drummond, L.J., and Sutherland, A.
• Subjects: Q Science > Q Science (General)
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• Publisher: Elsevier Ltd
• ISSN: 0040-4020
• ISSN (Online): 1464-5416
• Published Online: 09 June 2010