Enantioselective Organocatalytic Addition of Azlactones to Maleimides: A Highly Stereocontrolled Entry to 2,2-Disubstituted-2H-oxazol-5-ones

The first highly diastereo‐ and enantioselective organocatalytic synthesis of 2,2‐disubstituted‐2H‐oxazol‐5‐ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2‐disubstituted‐2H‐oxazol‐5‐ones with total regio‐...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-08, Vol.16 (32), p.9884-9889
Main Authors: Alba, Andrea-Nekane R., Valero, Guillem, Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert, Rios, Ramon
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Chemistry
maleimides
Michael addition
organocatalysis
oxazolones
Synthesis
Thioureas
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Summary:The first highly diastereo‐ and enantioselective organocatalytic synthesis of 2,2‐disubstituted‐2H‐oxazol‐5‐ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2‐disubstituted‐2H‐oxazol‐5‐ones with total regio‐ and stereocontrol. Thio‐E‐urea‐KA! The first highly diastereo‐ and enantioselective organocatalytic synthesis of 2,2‐disubstituted‐2H‐oxazol‐5‐ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2‐disubstituted‐2H‐oxazol‐5‐ones with total regio‐ and stereocontrol (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201000239