Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyl Compounds: Application to a Stereoselective Spirocyclization Sequence

被引：64

作者：

Boddaert, Thomas ^{[1
]}

Coquerel, Yoann ^{[1
]}

Rodriguez, Jean ^{[1
]}

机构：

[1] Aix Marseille Univ, Inst Sci Mol Marseille, CNRS, UMR 6263,ISM2,Ctr St Jerome,Serv 531, F-13397 Marseille 20, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 11-12期

关键词：

cross metathesis; Michael addition; N-heterocyclic carbenes; organocatalysis; spiro compounds; EFFICIENT;

D O I：

10.1002/adsc.200900292

中图分类号：

O69 [应用化学];

学科分类号：

070301 [无机化学];

摘要：

An eco-compatible diversity-oriented synthesis of alpha-spirolactones and alpha-spirolactams is described. The overall transformation involves an olefin cross-meta thesis followed by an intramolecular organocatalytic Michael-induced spirocyclization. Under microwave irradiation, the Hoveyda-Grubbs precatalyst can be iteratively used as the source of both the metathesis ruthenium-based catalyst, and the spirocyclization N-heterocyclic carbene catalyst.

引用

页码：1744 / 1748

页数：5

共 38 条

[1]

Irreversible cleavage of a carbene-rhodium bond in Rh-N-heterocyclic carbene complexes:: implications for catalysis [J].