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Synfacts 2010(1): 0104-0104
DOI: 10.1055/s-0029-1218493
DOI: 10.1055/s-0029-1218493
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Styrylisoxazoles as Cinnamate Equivalents
A. Baschieri, L. Bernardi*, A. Ricci, S. Suresh, M. F. A. Adamo*
Università di Bologna, Italy and Royal College of Surgeons, Dublin, Ireland
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2009 (online)
Significance
The authors use 4-nitro-5-styrylisoxazoles as acceptors in enantioselective Michael additions catalyzed by cinchonidine catalyst 1. Not only nitromethane but also secondary and tertiary nitroalkanes could be used. The reaction provides the corresponding Michael adducts in good to high yields and high enantioselectivities. The 4-nitro-5-styrylisoxazoles are stable solids and can be easily prepared in large quantities (10-100 mmol) from commercially available 3,5-dimethyl-4-nitroisoxazole and aromatic or heteroaromatic aldehydes.