Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

被引：31

作者：

Daniels, Blake E. ^{[1
]}

Ni, Jane ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 10期

基金：

加拿大自然科学与工程研究理事会; 美国国家卫生研究院;

关键词：

cyclizations; enantioselectivity; heterocycles; Lewis acids; zirconium; SILYL ENOL ETHERS; AZA-PRINS; ENANTIOSELECTIVE PROTONATION; TANDEM CATALYSIS; DOMINO REACTIONS; BRONSTED ACID; CYCLIZATIONS; PYRROLOINDOLINES; ACETALS; COPE;

D O I：

10.1002/anie.201510972

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl4 and 3,3-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl4BINOL complex serves as a chiral Lewis-acid-assisted BrOnsted acid.

引用

页码：3398 / 3402

页数：5

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