Metal-Catalyzed Directed Regio- and Enantioselective Ring-Opening of Epoxides

Accounts of Chemical Research
Chuan WangHisashi Yamamoto

Abstract

Control of regio- and stereoselectivity of chemical reactions is the central theme in synthetic chemistry. Regioselective and enantiospecific ring opening of readily available enantioenriched epoxides precursors provides a straightforward access to diverse highly functionalized molecules which can serve as chiral building blocks for synthesis of biologically active compounds. However, prior to our research work, the scope of catalytic highly regioselective ring opening of epoxides is limited to structurally or electronically biased epoxides, such as terminal and aromatic epoxides. Regioselective ring-opening of epoxides with substituents on both sides demonstrating similar steric and electronic effects is still a formidable challenge for organic chemists. To address this challenge, our approach is to use the readily available functional moiety incorporated in an epoxide as a directing group to realize the regioselective nucleophilic attack on the oxirane ring. Alternatively, asymmetric ring-opening of epoxides can also provide the ring-opening products in highly enantioenriched form. However, excellent results are usually obtained in the case of the kinetic resolution of terminal epoxides or the desymmetrization of meso-epoxide...Continue Reading

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Citations

May 18, 2017·Organic & Biomolecular Chemistry·Hélène Pellissier
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Shun-Ichiro UesugiYoshiharu Iwabuchi
Nov 5, 2016·Chemistry : a European Journal·Nico FunkenAndreas Gansäuer
Sep 28, 2018·Organic & Biomolecular Chemistry·Hongqing YaoChuan Wang
Feb 28, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Zhen LiuWenrong Yang
Nov 5, 2016·Angewandte Chemie·Hao JiangYong Huang
Apr 4, 2017·Chemical Communications : Chem Comm·Jan WenzLutz H Gade
Nov 12, 2020·Chemical Communications : Chem Comm·Yuan NiuShangdong Yang
Nov 17, 2020·Chemistry : a European Journal·Yuse KuriyamaYoshiharu Iwabuchi
Feb 28, 2018·The Journal of Organic Chemistry·Takahiro Sawano, Hisashi Yamamoto
Oct 21, 2020·The Journal of Organic Chemistry·Aran K Hubbell, Geoffrey W Coates
Aug 28, 2018·Organic Letters·Grace WangMark S Taylor
Mar 24, 2018·Chemical Reviews·Sukalyan Bhadra, Hisashi Yamamoto
Oct 1, 2021·Accounts of Chemical Research·Jason AnAmy R Howell

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