Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement

被引：193

作者：

Romanov-Michailidis, Fedor ^{[1
]}

Guenee, Laure ^{[2
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

[2] Univ Geneva, Crystallog Lab, CH-1211 Geneva 4, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 35期

基金：

新加坡国家研究基金会;

关键词：

anions; fluorine; organocatalysis; rearrangement; synthetic methods; PHASE-TRANSFER CATALYST; SEMIPINACOL REARRANGEMENT; MEDICINAL CHEMISTRY; ALPHA-FLUORINATION; ALLYLIC ALCOHOLS; BOND FORMATION; ALDEHYDES;

D O I：

10.1002/anie.201303527

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9266 / 9270

页数：5

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