Thiourea-Catalyzed Enantioselective Iso-Pictet-Spengler Reactions

被引：87

作者：

Lee, Yunmi ^{[1
]}

Klausen, Rebekka S. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 20期

关键词：

GAMMA-CARBOLINES; CONSTRUCTION; DERIVATIVES; ALKALOIDS; CHEMISTRY; HYDROGENATION; BIOSYNTHESIS; DISCOVERY; COGNITION; DIMEBON;

D O I：

10.1021/ol202300t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-gamma-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-protected products by trituration or crystallization provides the optically pure tetrahydro-gamma-carboline derivatives in a scalable and highly practical procedure.

引用

页码：5564 / 5567

页数：4

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