Diastereoselective Synthesis of Chiral 2,3-Disubstituted lndolines via Formal [3+2]-Cycloaddition of Arynes with γ-Amino-α,β-unsaturated Esters

被引：10
|
作者：
Aher, Ravindra D. [1 ]
Suryavanshi, Gurunath M. [1 ]
Sudalai, Arumugam [1 ]
机构：
[1] CSIR Natl Chem Lab, Chem Engn & Proc Dev Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 11期
关键词：
AZA-DIELS-ALDER; STEREOSELECTIVE-SYNTHESIS; CASCADE REACTIONS; INDOLINE; REARRANGEMENT; DERIVATIVES; ALKALOIDS; ROUTE; HYDROGENATION; CYCLOADDITION;
D O I：
10.1021/acs.joc.7b00439
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one step formal [3+2]-annulation protocol for the synthesis of 2,3-disubstituted indolines is described. The in situ generated aryne acts as a two-atom component, and gamma-amino-alpha,beta-unsaturated esters acting as a three-atom component to construct indoline units in a highly regio- and diastereoselective manner with yields ranging from 63 to 80%.
引用
收藏
页码：5940 / 5946
页数：7
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