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Convenient, large-scale asymmetric synthesis of β-aryl-substituted α,α-difluoro-β-amino acids

✍ Scribed by Vadim A Soloshonok; Hironari Ohkura; Alexander Sorochinsky; Natalia Voloshin; Andrey Markovsky; Michael Belik; Takashi Yamazaki

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 77 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01103-6

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✦ Synopsis

The enantiopure p-toluenesulfinimines were found to be efficient as chiral imine equivalents in the high temperature Reformatsky-type additions with BrZnCF 2 COOEt affording an efficient approach to the enantiomerically pure a,a-difluoro-bamino acids. High chemical and stereochemical yields (drs>9:1, and as high as 99:1) render this method immediately useful for preparing the target amino acids.

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