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Chalcogenide–Lewis Acid Mediated Tandem Michael Aldol Reaction — an Alternative to the Morita–Baylis–Hillman Reaction and a New Development
Author(s) -
Kataoka Tadashi,
Kinoshita Hironori
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400610
Subject(s) - chemistry , aldol reaction , baylis–hillman reaction , michael reaction , lewis acids and bases , triethylamine , nitroaldol reaction , stereocenter , heteroatom , organic chemistry , addition reaction , adduct , aldehyde , enantioselective synthesis , lewis acid catalysis , medicinal chemistry , stereochemistry , alkyl , catalysis
A tandem Michael aldol reaction mediated by a chalcogenide and Lewis acid was developed in three different types. Reactions of electron‐deficient alkenes with aldehydes or α‐keto esters in the presence of a sulfide and TiCl 4 gave α‐chloromethyl aldols. Reactions of chalcogenide–enones with carbonyl compounds gave α‐(α‐hydroxyalkyl)enones (Mori‐ta–Baylis–Hillman adducts) after the work‐up of the reaction mixture with triethylamine. The intramolecular Michael aldol reactions of N ‐enoylthioamides with aldehydes in the presence of BF 3 Et 2 O produced tricyclic compounds bearing a bridgehead bound to four heteroatoms and induced four stereocenters in one step, three of which were consecutive. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)