Enantioselective routes to (-)-(R)-muscone

被引：17

作者：

Bulic, Bruno ^{[1
]}

Luecking, Ulrich ^{[1
]}

Pfaltz, Andreas ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

SYNLETT | 2006年 / 07期

关键词：

macrocycles; copper; palladium; asymmetric catalysis; muscone;

D O I：

10.1055/s-2006-939069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The macrocyclic ring of muscone was prepared by Pd-catalyzed cyclization of hexadeca-1,15-diyne, which was converted to cyclopentadec-2-enone. The stereogenic center was introduced by enantioselective Cu-catalyzed conjugate addition of dimethyl-zinc. Because the ee in this step was only moderate, a new route via cyclopentadeca-2,14-dienone was developed. Enantioselective conjugate addition to this substrate led to 14-methylcylodec-2-enone, which was hydrogenated to give (-)-(R)-muscone in high overall yield with up to 98%

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页码：1031 / 1034

页数：4

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