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Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5

✍ Scribed by Fabio Piccinelli; Gianni Porzi; Monica Sandri; Sergio Sandri

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 206 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(02)00834-0

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✦ Synopsis

An efficient new stereocontrolled synthesis of (2R,6R)-(+)-and (2S,6S)-(-)-2,6-diamino-4-methylene-1,7-heptanedioic acid 8a and 9a, respectively, has been accomplished starting from the glycine-derived chiral synthon 1. The enantiomerically pure a-alkyl derivatives 8b-d and 9b-d have also been synthesized. The absolute configuration of the new stereocenters was assigned on the basis of 1 H NMR spectra.

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