Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate |
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Authors: | Sorochinsky Alexander Voloshin Natalia Markovsky Andrey Belik Michael Yasuda Nobuhiro Uekusa Hidehiro Ono Taizo Berbasov Dmitrii O Soloshonok Vadim A |
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Institution: | Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, Kiev-94, 253660, Ukraine. sorochinsky@bpci.kiev.ua |
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Abstract: | 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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