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Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate. | LitMetric
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Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate.

Alexander Sorochinsky Natalia Voloshin Andrey Markovsky Michael Belik Nobuhiro Yasuda Hidehiro Uekusa Taizo Ono Dmitrii O Berbasov Vadim A Soloshonok

J Org Chem

Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, Kiev-94, 253660, Ukraine.

Published: September 2003

The enantiopure Davis' N-sulfinylimines 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 alpha,alpha-difluoro-beta-amino 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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http://dx.doi.org/10.1021/jo030082kDOI Listing

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