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Enantioselective Organocatalytic Addition of Azlactones to Maleimides: A Highly Stereocontrolled Entry to 2,2‐Disubstituted‐2 H ‐oxazol‐5‐ones
Author(s) -
Alba AndreaNekane R.,
Valero Guillem,
Calbet Teresa,
FontBardía Mercé,
Moyano Albert,
Rios Ramon
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000239
Subject(s) - enantioselective synthesis , bifunctional , thiourea , organocatalysis , chemistry , organic chemistry , catalysis
The first highly diastereo‐ and enantioselective organocatalytic synthesis of 2,2‐disubstituted‐2 H ‐oxazol‐5‐ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2‐disubstituted‐2 H ‐oxazol‐5‐ones with total regio‐ and stereocontrol.