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- Title
Organocatalytic conjugate addition of nitroalkanes to 2H-chromene-3-carbaldehydes: synthesis of highly functionalized chroman derivatives.
- Authors
Jun-min Zhang; Chun-liang Lou; Zhi-peng Hu; Ming Yan
- Abstract
Conjugate addition of nitroalkanes to 2H-chromene-3-carbaldehydes has been studied using a number of amines as the catalysts. Prolinol triethylsilyl ether was found to be the best catalyst for the reaction. The use of protonic solvents was also important. The reaction of variously substituted 2H-chromene-3-carbaldehydes with nitromethane afforded the products with excellent yields and diastereoselectivities. Nitroethane and 1-nitropropane were also applicable, however in decreased yields. The enantioselectivities of the reaction were very low and almost racemic products (3∼5% ee) were obtained in all cases. The reaction provides a new method for the preparation of highly functionalized chroman derivatives.
- Subjects
NITROALKANES; NITROMETHANE; TARTARIC acid; NITROPROPANE; ESTROGEN antagonists; OXIDATION; KETONES; ALDEHYDES; BENZOIC acid
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2009, p362
- ISSN
1551-7004
- Publication type
Article