Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis

被引：143

作者：

Leth, Lars A. ^{[1
]}

Glaus, Florian ^{[1
]}

Meazza, Marta ^{[1
]}

Fu, Liang ^{[1
]}

Thogersen, Mathias K. ^{[1
]}

Bitsch, Emma A. ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 49期

关键词：

asymmetric catalysis; cycloaddition; decarboxylation; heterocycles; synergistic catalysis; TRANSITION-METAL CATALYSIS; ALPHA-ALLYLATION; ASYMMETRIC AMINOCATALYSIS; VINYL CYCLOPROPANES; ENAMINE CATALYSIS; ALDEHYDES; STEREOCENTERS; CONSTRUCTION; REACTIVITIES; CYCLIZATIONS;

D O I：

10.1002/anie.201607788

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis has been developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated ,-unsaturated aldehydes. The reaction is demonstrated to proceed for a number of combinations of vinyl benzoxazinanones reacting with ,-unsaturated aldehydes, providing highly substituted vinyl tetrahydroquinolines in good to high yields, and excellent enantio- and diastereoselectivities (>98% ee and >20:1 d.r.). The palladium catalyst used in the synergistic catalysis can be re-used in a one-pot sequential coupling reaction with an aromatic boronic acid forming the coupling product in 95% yield, >20:1 d.r. and 99% ee.

引用

页码：15272 / 15276

页数：5

共 43 条

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