Synthesis of dehydro-β-amino esters via highly regioselective amination of allylic carbonates

被引：31

作者：

Benfatti, Fides ^{[1
]}

Cardillo, Giuliana ^{[1
]}

Gentilucci, Luca ^{[1
]}

Mosconi, Elisa ^{[1
]}

Tolomelli, Alessandral ^{[1
]}

机构：

[1] Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol8006919

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism. On the other hand, under palladium-catalyzed conditions, the reaction shows a strong solvent-dependent regiocontrol, affording exclusively one of the two possible regioisomers with complete transfer of chirality from the substrates to the products.

引用

页码：2425 / 2428

页数：4

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