Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols

Journal of the American Chemical Society
Dennis X HuNoah Z Burns

Abstract

Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.

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Citations

Sep 24, 2015·Journal of the American Chemical Society·Cyril BucherNoah Z Burns
Mar 29, 2016·Journal of the American Chemical Society·Matthew L LandryNoah Z Burns
Sep 24, 2016·Organic Letters·Minxing ShenScott A Snyder
Jan 28, 2017·Organic Letters·Yeshua Sempere MolinaErick M Carreira
Jan 24, 2017·Journal of the American Chemical Society·Bardia SoltanzadehBabak Borhan
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Dec 3, 2015·Angewandte Chemie·Alexander J CresswellScott E Denmark
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Frederick J Seidl, Noah Z Burns
Jan 22, 2020·Organic & Biomolecular Chemistry·Renzhi ChenYandong Zhang
Dec 6, 2019·Chemistry : a European Journal·Huanfeng JiangFulin Chen
Oct 31, 2015·Chemistry : a European Journal·Dan LehnherrWilliam R Dichtel
Feb 3, 2016·Angewandte Chemie·Won-jin Chung, Christopher D Vanderwal
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Mar 24, 2018·Chemical Reviews·Sukalyan Bhadra, Hisashi Yamamoto
Aug 14, 2018·Journal of the American Chemical Society·Yi-Ming CaoMathias Christmann
Sep 1, 2017·Journal of the American Chemical Society·Alexander J BurckleNoah Z Burns
Aug 21, 2021·Journal of the American Chemical Society·Taeho KangKeary M Engle
Sep 20, 2017·Journal of the American Chemical Society·Cristina García-MoralesAntonio M Echavarren
Apr 17, 2018·Journal of the American Chemical Society·Xiaowei WuJohn A Porco
Apr 18, 2018·Accounts of Chemical Research·Matthew L Landry, Noah Z Burns

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