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Dysprosium(III)‐Catalyzed Ring‐Opening of meso ‐Epoxides: Desymmetrization by Remote Stereocontrol in a Thiolysis/Elimination Sequence
Author(s) -
Yao Lu,
Zhu Qiao,
Wei Liang,
Wang ZuoFei,
Wang ChunJiang
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601083
Subject(s) - desymmetrization , stereocenter , cyclopentene , chemistry , enantioselective synthesis , thiolysis , ring (chemistry) , catalysis , stereochemistry , combinatorial chemistry , yield (engineering) , organic chemistry , polyphenol , materials science , proanthocyanidin , metallurgy , antioxidant
An unprecedented asymmetric desymmetrization of meso ‐epoxides, derived from cyclopentene‐1,3‐diones, with 2‐mercaptobenzothiazoles has been realized. It was efficiently catalyzed by a chiral Dy III /N,N′‐dioxide complex through a thiolysis/elimination sequence. This remote stereocontrol strategy provides facile access to synthetically versatile cyclopentene derivatives bearing an all‐carbon quaternary stereogenic center in high yield and excellent enantioselectivity. Intriguingly, optically active thiophene could be readily generated from the obtained product through an efficient one‐pot protocol.