ASYMMETRIC HYDROGENATION OF 3,5-DIOXOESTERS CATALYZED BY RU-BINAP COMPLEX - A SHORT STEP ASYMMETRIC-SYNTHESIS OF 6-SUBSTITUTED 5,6-DIHYDRO-2-PYRONES

被引：78

作者：

SHAO, LM ^{[1
]}

KAWANO, H ^{[1
]}

SABURI, M ^{[1
]}

UCHIDA, Y ^{[1
]}

机构：

[1] UNIV TOKYO,FAC ENGN,DEPT IND CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 10期

关键词：

3,5-DIOXOESTER; RU-BINAP CATALYST; ASYMMETRIC HYDROGENATION; ASYMMETRIC SYNTHESIS; LACTONE;

D O I：

10.1016/S0040-4020(01)86300-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.

引用

页码：1997 / 2010

页数：14

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