Switchable Diastereoselectivity in Enantioselective [4+2] Cycloadditions with Simple Olefins by Asymmetric Binary Acid Catalysis

被引：87

作者：

Lv, Jian ^{[1
]}

Zhang, Long ^{[1
]}

Luo, Sanzhong ^{[1
]}

Cheng, Jin-Pei ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 37期

关键词：

asymmetric catalysis; binary catalysts; diastereoselectivity; Diels-Alder reaction; olefins; DIELS-ALDER REACTIONS; CHIRAL PHOSPHORIC-ACID; BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; FRIEDEL-CRAFTS REACTIONS; RECENT PROGRESS; ESTERS; HETEROCYCLOADDITION; DIARYLHEPTANOIDS; DIHYDROPYRANS; CONSTRUCTION;

D O I：

10.1002/anie.201304561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The exchange of the metal ion from InIII to ScIII in a binary acid catalyst leads to a switch in the diastereoselectivity of [4+2] cycloadditions. Simple olefins and β,γ-unsaturated α-ketoester were thus transformed to the corresponding exo or endo products, respectively, with excellent diastereoselectivity (up to 99:1 d.r.) and enantioselectivity (up to 99 % ee). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9786 / 9790

页数：5

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