The first highly enantioselective alkynylation of chloral: A practical and efficient pathway to chiral trichloromethyl propargyl alcohols

被引：38

作者：

Jiang, B ^{[1
]}

Si, YG ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 06期

关键词：

1,2-amino alcohols; chloral; enantioselective alkynylation; N; O ligands; propargyl alcohols; zinc;

D O I：

10.1002/adsc.200303237

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new, inexpensive chiral amino alcohol-based ligand, (1S,2S)-2-N,N-dimethylamino-1-(4-nitrophenyl)-3-(tert-butyloxy)propan-1-ol, was developed for the asymmetric alkynylation of chloral in high yield with up to 98% ee. The resulting chiral adduct (S)-1-trichloromethyl-3-phenyl-2-propyn-1-ol was hydrogenated over 10% Pd/C to give the useful intermediate chiral trichloromethyl carbinol in quantitative yield, which was efficiently transformed into the pharmaceutically important building blocks 2-hydroxy-4-phenylbutanoate and homophenylalanine in high yield with excellent enantiomeric excess.

引用

页码：669 / 674

页数：6

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