Asymmetric Diels-Alder, Michael, and Aldol reactions using a planar chiral 1,3-oxazol-2(3H)-one derived from (R)-(+)-4-hydroxy-[2.2]paracyclophane

被引：32

作者：

Cipiciani, A ^{[1
]}

Fringuelli, F ^{[1
]}

Piermatti, O ^{[1
]}

Pizzo, F ^{[1
]}

Ruzziconi, R ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 08期

关键词：

D O I：

10.1021/jo016383g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of alpha,beta-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face- diastereoselectivity is good and is controlled by the spatial relationship between the prochiral center and the C9-C10 ethylene bridge of the [2.2]paracyclophane moiety. The chiral auxiliary is easily removed and quantitatively recovered.

引用

页码：2665 / 2670

页数：6

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