Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Diels-Alder reaction sequence affording rapid entry to polycyclic compounds

被引：50

作者：

Brummond, KM ^{[1
]}

You, LF ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 26期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

Rh(I) allenic Alder ene; Diels-Alder reaction; consecutive transition metal catalyzed rections; allenynes; polycycles; cross-conjugated trienes;

D O I：

10.1016/j.tet.2005.03.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conversion of acyclic allenynes to polycyclic compounds using consecutive transition metal catalyzed carbon-carbon bond formin, reactions in a single chemical operation is described. Reaction of an allenyne with a Rh(1) catalyst affords a cross-conjugated triene via a formal Alder-ene reaction. The triene then participates in a Rh(1)-catalyzed intramolecular [4+2] cycloaddition reaction to generate a new conjugated diene. An external dienophile is added to this diene which then undergoes a second [4+2] cycloaddition reaction to afford a complex polycyclic ring system. This reaction sequence demonstrates the synthetic potential of allenynes and cross conjugated trienes and highlights the rapid increases in molecular complexity that are possible by one-pot sequential transition metal catalyzed carbon-carbon bond forming reactions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6180 / 6185

页数：6

共 28 条

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