Issue 18, 2005

A short, versatile chemical synthesis of l- and d-amino acids stereoselectively labelled solely in the beta position

Abstract

L- and D-Amino acids which are stereoselectively labelled solely either in the 3-pro-R or in the 3-pro-S-positions have been prepared by a relatively short chemical synthesis in ee of 81 to 86%. This involves Sharpless' aminohydroxylation and cyclisation with inversion of stereochemistry at C-2 to give the stereoselectively labelled D- and L-aziridines 10a and 10b, and 8a and 8b. These have previously been modified and cleaved with inversion of stereochemistry at C-3 using a number of nucleophiles to give a large variety of protected amino acids. Synthesis of the labelled D- and L-β-chloroalanines 22a and 22b and 25a and 25b is described here.

Graphical abstract: A short, versatile chemical synthesis of l- and d-amino acids stereoselectively labelled solely in the beta position

Article information

Article type
Paper
Submitted
10 Jun 2005
Accepted
05 Jul 2005
First published
15 Aug 2005

Org. Biomol. Chem., 2005,3, 3348-3356

A short, versatile chemical synthesis of L- and D-amino acids stereoselectively labelled solely in the beta position

K. Lowpetch and D. W. Young, Org. Biomol. Chem., 2005, 3, 3348 DOI: 10.1039/B508196C

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