Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates

被引：36

作者：

Cerveri, Alessandro ^{[1
]}

Nieto Faza, Olalla ^{[2
]}

Silva Lopez, Carlos ^{[2
]}

Grilli, Stefano ^{[1
]}

Monari, Magda ^{[1
]}

Bandini, Marco ^{[1
]}

机构：

[1] Alma Mater Studiorum Univ Bologna, Dipartimento Chim G Ciamician, Via Selmi 2, I-40126 Bologna, Italy

[2] Univ Vigo, Dept Quim Organ, Vigo 36310, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 10期

关键词：

3+2 CYCLOADDITION; ASYMMETRIC DEAROMATIZATION; 1,3-DIPOLAR CYCLOADDITION; NUCLEOPHILIC-ADDITION; 3-NITROINDOLES; INDOLES; ACCESS; 2,3-BUTADIENOATES; 2-BUTYNOATES; ALLENAMIDES;

D O I：

10.1021/acs.joc.9b00559

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective phosphine-catalyzed ((pMeOC(6)H(4))(3)P, 10-20 mol %) dearomatization of 3-NO2-indoles with allenoates is described. A range of densely functionalized indolines (18 examples) is obtained in high yields (up to 96%) under mild reaction conditions (rt, air, reagent-grade solvent). Computational simulations and labeling experiments revealed a stepwise [3 + 2]-type mechanism involving a water-assisted hydrogen shift and accounted for the diastereoselection recorded.

引用

页码：6347 / 6355

页数：9

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