文献类型：期刊文献

英文题名：Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides

作者：Zhu, Rui-Heng[1];Shi, Xiao-Xin[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China

年份：2011

卷号：22

期号：4

起止页码：387

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000290075100003)，CCR-EXPANDED(收录号:WOS:000290075100003)】；

基金：We thank the National Natural Science Foundation of China (No. 20972048) and the Shanghai Educational Development Foundation (The Dawn Program: No. 03SG27) for the financial support of this work.

语种：英文

摘要：A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.