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
收藏
页码：1826 / 1829
页数：4
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