通过戴维斯的N-亚磺酰亚胺与溴二氟乙酸乙酯之间的瑞福马斯基反应便捷地不对称合成β-取代的α,α-二氟-β-氨基酸。
Convenient asymmetric synthesis of beta-substituted alpha,alpha-difluoro-beta-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate.
作者信息
Sorochinsky Alexander, Voloshin Natalia, Markovsky Andrey, Belik Michael, Yasuda Nobuhiro, Uekusa Hidehiro, Ono Taizo, Berbasov Dmitrii O, Soloshonok Vadim A
机构信息
Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, Kiev-94, 253660, Ukraine.
出版信息
J Org Chem. 2003 Sep 19;68(19):7448-54. doi: 10.1021/jo030082k.
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.
对映体纯的戴维斯N-亚磺酰亚胺被发现可作为手性亚胺等价物，用于与BrZnCF(2)COOEt进行高温Reformatsky型加成反应，为对映体纯的α,α-二氟-β-氨基酸提供了一种有效方法。高化学产率和立体化学产率（非对映体比例>9:1，高达99:1）使该方法可立即用于制备目标氨基酸。
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