Stereoselective reduction of enantiopure beta-enamino esters by hydride: A convenient synthesis of both enantiopure beta-amino esters

被引：146

作者：

Cimarelli, C ^{[1
]}

Palmieri, G ^{[1
]}

机构：

[1] UNIV CAMERINO,DIPARTIMENTO SCI CHIM,I-62032 CAMERINO,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 16期

关键词：

D O I：

10.1021/jo960107y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.

引用

页码：5557 / 5563

页数：7

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