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- Title
Dysprosium(III)-Catalyzed Ring-Opening of meso-Epoxides: Desymmetrization by Remote Stereocontrol in a Thiolysis/Elimination Sequence.
- Authors
Yao, Lu; Zhu, Qiao; Wei, Liang; Wang, Zuo ‐ Fei; Wang, Chun ‐ Jiang
- Abstract
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 DyIII/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.
- Subjects
EPOXY compounds; CYCLOPENTENES; ENANTIOSELECTIVE catalysis; THIOPHENES; CHEMICAL derivatives
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 19, p5923
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201601083