Highly enantioselective electrophilic amination and michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox:: The mechanism

被引：85

作者：

Comelles, Josep

Pericas, Alex

Moreno-Manas, Marcial

Vallribera, Adelina ^{[1
]}

Drudis-Sole, Gali

Lledos, Agusti

Parella, Teodor

Roglans, Anna

Garcia-Granda, Santiago

Roces-Fernandez, Laura

机构：

[1] Univ Autonoma Barcelona, Dept Chem, Barcelona 08193, Spain

[2] Univ Girona, Dept Chem, Girona 17071, Spain

[3] Univ Oviedo, Dept Quim Fis & Analit, E-33006 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 06期

关键词：

D O I：

10.1021/jo0622678

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High enantioselection is obtained in Michael additions of cyclic beta-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and beta-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.

引用

页码：2077 / 2087

页数：11

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