Palladium-catalyzed oxidative wacker cyclizations in nonpolar organic solvents with molecular oxygen: A stepping stone to asymmetric aerobic cyclizations

被引：220

作者：

Trend, RM ^{[1
]}

Ramtohul, YK ^{[1
]}

Ferreira, EM ^{[1
]}

Stoltz, BM ^{[1
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 25期

关键词：

asymmetric catalysis; homogeneous catalysis; oxidation; oxygen; palladium;

D O I：

10.1002/anie.200351196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of Pd-catalyzed oxidative nucleophile/alkene cyclizations proceeds in excellent yield under simple aerobic conditions in nonpolar media (Pd catalyst, pyridine, and O2 in toluene). Nucleophiles for these cyclizations include phenols, carboxylic acids, amides, and primary alcohols. Additionally, enantioselective catalysis is feasible with a Pd-sparteine system (see picture). Enantioselectivities of up to 90% ee are observed for simple phenol/alkene cyclizations.

引用

页码：2892 / 2895

页数：4

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