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Lewis Base/Brønsted Acid Co-catalyzed Enantioselective Sulfenylation/Semipinacol Rearrangement of Di- and Trisubstituted Allylic Alcohols.

Authors :
Xie YY
Chen ZM
Luo HY
Shao H
Tu YQ
Bao X
Cao RF
Zhang SY
Tian JM
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Sep 02; Vol. 58 (36), pp. 12491-12496. Date of Electronic Publication: 2019 Aug 07.
Publication Year :
2019

Abstract

An enantioselective sulfenylation/semipinacol rearrangement of 1,1-disubstituted and trisubstituted allylic alcohols was accomplished with a chiral Lewis base and a chiral Brønsted acid as cocatalysts, generating various β-arylthio ketones bearing an all-carbon quaternary center in moderate to excellent yields and excellent enantioselectivities. These chiral arylthio ketone products are common intermediates with many applications, for example, in the design of new chiral catalysts/ligands and the total synthesis of natural products. Computational studies (DFT calculations) were carried out to explain the enantioselectivity and the role of the chiral Brønsted acid. Additionally, the synthetic utility of this method was exemplified by an enantioselective total synthesis of (-)-herbertene and a one-pot synthesis of a chiral sulfoxide and sulfone.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
58
Issue :
36
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
31293063
Full Text :
https://doi.org/10.1002/anie.201907115