Phosphine-mediated [4+2] annulation of bis(enones):: A Lewis base catalyzed "mock Diels-Alder" reaction

被引：27

作者：

Couturier, M ^{[1
]}

Ménard, F ^{[1
]}

Ragan, JA ^{[1
]}

Riou, M ^{[1
]}

Dauphin, E ^{[1
]}

Andresen, BM ^{[1
]}

Ghosh, A ^{[1
]}

Dupont-Gaudet, K ^{[1
]}

Girardin, M ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 11期

关键词：

D O I：

10.1021/ol049392v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a trialkylphosphine mediates both bond formation steps in two distinct catalytic cycles. The single-pot operation generates two carbon-carbon bonds and up to five contiguous stereocenters in one step, starting from achiral, aliphatic substrates; eight examples are provided.

引用

页码：1857 / 1860

页数：4

共 37 条

[21] ON THE ASYMMETRIC RH(I) CATALYZED [4+2] CYCLOISOMERIZATION REACTION - ELECTRONIC AND TORSIONAL LIGAND CONTROL OF ABSOLUTE STEREOSELECTION [J].