Diastereoselective addition reactions of furyl sulfonylimine using chiral boronates as auxiliary: Application to the enantioselective synthesis of 2,3-disubstituted furyl sulfonylamides

被引：35

作者：

Yim, HK

Wong, HNC ^{[1
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[2] Chinese Univ Hong Kong, Inst Chinese Med, Shatin, Hong Kong, Peoples R China

[3] Chinese Univ Hong Kong, Cent Lab, Inst Mol Technol Drug Discovery & Synth, Shatin, Hong Kong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 08期

关键词：

D O I：

10.1021/jo030385e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition reactions of various nucleophiles to a furyl sulfonylimine bearing a chiral boronate at the C-3 position furnished chromatographically separable diastereomers. The R diastereoselection was found to be more favorable. Further transformation of C-B bonds to C-C bonds was achieved by using standard Suzuki coupling conditions to give optically active 2,3-disubstituted furyl sulfonylamides.

引用

页码：2892 / 2895

页数：4

共 28 条

[1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].