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Organocatalytic Domino Michael–Heterocyclization Reaction of α,β‐Unsaturated Aldehydes and α‐Cyano Ketones: Synthesis of Enantioenriched 4,5,6‐Trisubstituted 3,4‐Dihydropyranones
Author(s) -
GuevaraPulido James O.,
Andrés José M.,
Pedrosa Rafael
Publication year - 2014
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.201402982
Subject(s) - chemistry , substituent , domino , michael reaction , polar effect , organic chemistry , carbonyl group , medicinal chemistry , catalysis
α,β‐Unsaturated aldehydes with aliphatic, electron‐poor aromatic, or electron‐withdrawing substituents at the β position easily react with different ketones leading to enantioenriched hemiacetals, which were further oxidized to give 4,5,6‐trisubstituted‐3,4‐dihydropyranones in good yields and with excellent enantioselectivities. The behavior of the ketones is dependent on the α substituent of the carbonyl group, and a fine‐tuning of the p K a values is necessary to obtain good results.