Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans
OA Location
Author(s)
Belmessieri, Dorine
de la Houpliere, Alix
Calder, Ewen DD
Taylor, James E
Smith, Andrew D
Type
Journal Article
Abstract
A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)‐(−)‐tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r.syn/anti, 99 % eesyn), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti‐diastereoisomers as the major product (up to 10:90 d.r.syn/anti, 99 % eeanti).
Date Issued
2014-07-28
Date Acceptance
2014-07-01
Citation
Chemistry: A European Journal, 2014, 20 (31), pp.9762-9769
ISSN
0947-6539
Publisher
Wiley
Start Page
9762
End Page
9769
Journal / Book Title
Chemistry: A European Journal
Volume
20
Issue
31
Copyright Statement
© 2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000340176600040&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
asymmetric catalysis
cinchona alkaloid
isothiourea
Michael addition
organocatalysis
oxygen heterocycles
stereodivergent
ONE-POT SYNTHESIS
CATALYZED ALDOL-LACTONIZATION
TRICYCLIC BETA-LACTONES
ENANTIOSELECTIVE SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
KINETIC RESOLUTION
RECENT PROGRESS
DERIVATIVES
BENZOTETRAMISOLE
ANHYDRIDES
Publication Status
Published
Date Publish Online
2014-07-02