Stereoselective Synthesis of Isoquinuclidines through an Aza-[4+2] Cycloaddition of Chiral Cyclic 2-Amidodienes

被引：9

作者：

Fang, Li-Chao ^{[1
]}

Hsung, Richard P. ^{[1
]}

机构：

[1] Univ Wisconsin, Sch Pharm, Div Pharmaceut Sci, Madison, WI 53705 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 06期

关键词：

DIELS-ALDER REACTIONS; XESTOCYCLAMINE-A; DAPHNIPHYLLUM ALKALOIDS; EFFICIENT; IMINES; RING; (+/-)-CATHARANTHINE; 2-AMIDO-DIENES; ALLENAMIDES; ROUTE;

D O I：

10.1021/ol500390a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents an unexpected switch from the anticipated endo-I selectivity obtained in the all-carbon cycloaddition.

引用

页码：1826 / 1829

页数：4

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