Matching the Chirality of Monodentate N-Heterocyclic Carbene Ligands: A Case Study on Well-Defined Palladium Complexes for the Asymmetric α-Arylation of Amides

被引：107

作者：

Luan, Xinjun ^{[1
]}

Mariz, Ronaldo ^{[1
]}

Robert, Carine ^{[1
]}

Gatti, Michele ^{[1
]}

Blumentritt, Sascha ^{[1
]}

Linden, Anthony ^{[1
]}

Dorta, Reto ^{[1
]}

机构：

[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 24期

关键词：

D O I：

10.1021/ol8021808

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbene ligands derived from C-2-symmetric diamines with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)CI are prepared. These compounds exist as a mixture of diastereomers, and the palladium complexes can be successfully separated and their absolute stereochemistry assigned. When used in the asymmetric intramolecular alpha-arylation of amides, oxindoles with quaternary carbon centers can be obtained in high yield and selectivity when correctly matching the chirality of the NHC complexes.

引用

页码：5569 / 5572

页数：4

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