Stereoselective synthesis of the antibacterial 3-fluoro-D-alanine

被引：23

作者：

Bravo, P ^{[1
]}

Cavicchio, G ^{[1
]}

Crucianelli, M ^{[1
]}

Poggiali, A ^{[1
]}

Zanda, M ^{[1
]}

机构：

[1] UNIV AQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67010 COPPITO,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(97)00334-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：2811 / 2815

页数：5

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