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
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
收藏
页码:1981 / 1985
页数:5
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