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Chiral Bifunctional Thiourea–Phosphane Organocatalysts in Asymmetric Allylic Amination of Morita–Baylis–Hillman Acetates
Author(s) -
Deng HongPing,
Wei Yin,
Shi Min
Publication year - 2011
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.201001660
Subject(s) - chemistry , allylic rearrangement , bifunctional , amination , thiourea , methyl vinyl ketone , organic chemistry , ketone , baylis–hillman reaction , catalysis , enantioselective synthesis , organocatalysis , medicinal chemistry
A series of new chiral bifunctional thiourea–phosphane catalysts was synthesized and successfully applied in the catalytic, asymmetric allylic amination of Morita–Baylis–Hillman (MBH) acetates derived from the methyl vinyl ketone (MVK) or ethyl vinyl ketone (EVK) system, with phthalimide, affording the amination products in up to over 99 % yield and 90 % ee for a wide range of substrates derived from different aromatic aldehydes.