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Preparation and Transmetallation of Enantioenriched α-Aminoorganostannanes Derived from N-Boc Phenylglycinol: Application to the Synthesis of Alafosfalin

✍ Scribed by Vincent Coeffard; Isabelle Beaudet; Michel Evain; Erwan Le Grognec; Jean-Paul Quintard

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 358 KB
Volume: 2008
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200800208

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✦ Synopsis

Abstract

Enantioenriched tributylstannylated α‐amino alcohols were synthesised by an improved procedure based on ring opening of 2‐tributylstannyloxazolidines. Corresponding α‐amino organolithiums were generated from O‐silylated tributylstannylated α‐amino alcohols and trapped with retention of configuration. Thereby, this methodology was used to synthesise the antibacterial α‐aminophosphonic acid alafosfalin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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