α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids

被引：19

作者：

Cardillo, G ^{[1
]}

Fabbroni, S ^{[1
]}

Gentilucci, L ^{[1
]}

Perciaccante, R ^{[1
]}

Tolomelli, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期

关键词：

D O I：

10.1016/j.tetasy.2003.12.029

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of alpha-benzylamino-beta,gamma-unsaturated acids has been developed starting from alpha-bromo-alpha,beta-unsaturated chlorides. Via treatment of the acyl chlorides with (R)-pantolactone in the presence of TEA, the in situ formation of the deconjugated ketenes and their direct transformation into chiral esters was performed. The substitution of bromine with benzylamine, followed by acid hydrolysis, allowed to us obtain enantionterically enriched alpha-benzylamino-beta,gamma-unsaturated acids. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：593 / 601

页数：9

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