Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents

被引：52

作者：

Davis, FA ^{[1
]}

Fanelli, DL ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 06期

关键词：

D O I：

10.1021/jo972076s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.

引用

页码：1981 / 1985

页数：5

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[21] A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS [J].