Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines via the Diels-Alder Reaction

被引：44

作者：

Martin, Rhia M. ^{[1
]}

Bergman, Robert G. ^{[2
,3
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA

[3] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 03期

关键词：

STEREOSELECTIVE-SYNTHESIS; HYDROISOQUINOLINE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CHIRAL ISOQUINUCLIDINES; CYCLOADDITION REACTIONS; GROB FRAGMENTATION; MANNICH APPROACH; IBOGA ALKALOIDS; 1,2-DIHYDROPYRIDINE; DERIVATIVES;

D O I：

10.1021/ol303040r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities.

引用

页码：444 / 447

页数：4

共 76 条

[31] Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].