Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination

被引：31

作者：

Bizet, Vincent ^{[1
]}

Borrajo-Calleja, Gustavo M. ^{[1
]}

Besnard, Celine ^{[2
]}

Mazet, Clement ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, 30 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

[2] Univ Geneva, Crystallog Lab, 24 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

来源：

ACS CATALYSIS | 2016年 / 6卷 / 10期

基金：

瑞士国家科学基金会;

关键词：

palladium catalysis; cross-coupling; intermolecular carboamination; furoindolines; enantioselective catalysis; diastereoselective catalysis; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC ARYLATION; GAMMA-ARYLATION; HECK REACTIONS; PHOSPHINE; DEAROMATIZATION; LIGANDS; VINYLATION; ACIDITIES; ALKALOIDS;

D O I：

10.1021/acscatal.6b02238

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A versatile Pd-catalyzed intermolecular syncarboamination of dihydrofurans giving access to the ubiquitous furoindoline motif is described. The efficiency of the process relies on the use of Buchwald-type biarylphosphines and the perfect control for site-selectivity of Pd insertion across the C=C bond. A catalytic sequence consisting of Heck and carboamination cross-coupling reactions from readily available dihydrofurans affords-in usually high chemical yields and high levels of diastereocontrol-poly(hetero)cyclic compounds that would be difficult to access by established methods. Encouraging preliminary results for the enantioselective carboamination of 2,3-dihydrofurans are also disclosed.

引用

页码：7183 / 7187

页数：5

共 68 条

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