Aerobic Radical-Cascade Alkylation/Cyclization of α,β-Unsaturated Amides: an Efficient Approach to Quaternary Oxindoles

被引：104

作者：

Biswas, Promita ^{[1
]}

Paul, Subhasis ^{[1
]}

Guin, Joyram ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, 2A & 2B Raja SC Mullick Rd, Kolkata 700032, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 27期

关键词：

alkylation; cascade reactions; cyclization; oxindoles; radical reactions; CATALYTIC ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCT SYNTHESIS; C-H FUNCTIONALIZATION; ARYL C(SP(2))-H BONDS; ACETIC-ACID SOLUTION; METAL-FREE SYNTHESIS; ACTIVATED ALKENES; ALZHEIMERS-DISEASE; N-ARYLACRYLAMIDES; AROMATIC-ALDEHYDES;

D O I：

10.1002/anie.201603809

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the aerobic radical-cascade alkylation/cyclization of alpha,beta-unsaturated amides to afford functionalized oxindoles with a C3 quaternary stereocenter is described. The process is based on the generation of valuable alkyl radicals through sustainable aerobic C-H activation of aldehydes followed by decarbonylation using O-2 as the sole oxidant. This method features a broad substrate scope, inexpensive alkyl radical precursors, and convenient reagents. Finally, the method was successfully applied to the synthesis of alkyl analogues of tetrahydrofuranoindoline and (+/-)-esermethole.

引用

页码：7756 / 7760

页数：5

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