p-Menthane-3-carboxaldehyde:: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity

被引：44

作者：

Spino, C ^{[1
]}

Godbout, C ^{[1
]}

Beaulieu, C ^{[1
]}

Harter, M ^{[1
]}

Mwene-Mbeja, TM ^{[1
]}

Boisvert, L ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 41期

关键词：

D O I：

10.1021/ja046084j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(+)- or (-)-p-Menthane-3-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a a-chiral quaternary carbon. The flexibility, efficiency, and ease of use of the method are demonstrated in a series of examples, which include the total synthesis of (+)-cuparenone as well as a partial synthesis of (-)-cassiol.

引用

页码：13312 / 13319

页数：8

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