Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

被引：36

作者：

Andrews, PC

Bhaskar, V

Bromfield, KM

Dodd, AM

Duggan, PJ ^{[1
]}

Duggan, SAM

McCarthy, TD

机构：

[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia

[2] Monash Univ, Ctr Green Chem, Melbourne, Vic 3800, Australia

[3] Biomol Res Inst, Melbourne, Vic 3169, Australia

来源：

SYNLETT | 2004年 / 05期

关键词：

beta-amino acids; diastereoselectivity; lithium amides; conjugate additions; fluorination;

D O I：

10.1055/s-2004-817782

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Amino-a-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-alpha-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (2S,3S)-alpha-fluoro-beta-phenylalanine followed by Fmoc protection was achieved.

引用

页码：791 / 794

页数：4

共 20 条

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