ENANTIOSELECTIVE SYNTHESIS OF SPIRO[4.5]DECANONE WITH 2-(S)-METHOXY-1,4-DIBROMOBUTANE

被引：18

作者：

GALVEZ, JMG ^{[1
]}

ANGERS, P ^{[1
]}

CANONNE, P ^{[1
]}

机构：

[1] UNIV LAVAL,DEPT CHIM,ST FOY G1K 7P4,PQ,CANADA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

ALKYLATION; CHIRAL DIBROMIDE; DIISOPROPOXYDIMETHYLTITANIUM; CATALYTIC HYDROGENATION; ASYMMETRIC SPIROANNELATION;

D O I：

10.1016/S0040-4039(00)76641-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 3-methyl-2-cyclohexen-1-one with 2-(S)-methoxy-1,4-dibromobutane (2) produced spiro[4.5]decanone 3, a key intermediate for the synthesis of spirovetivanes, with regiodifferentiation and stereoselection. Subsequent addition of diisopropoxydimethyltitanium to the carbonyl group furnished compound 6 with diasterofacial selectivity. The same selectivity was observed in the subsequent catalytic hydrogenation.

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页码：2849 / 2852

页数：4

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