title: Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic, and direct michael reaction of nitroethanol with alpha,beta-unsaturated aldehydes.
abstract: Diphenylprolinol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and alpha,beta-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4-disubstituted tetrahydropyrans after isomerization. The generated Michael addition products are useful synthetic intermediates, which can be converted into chiral tetrahydropyran with a quaternary stereocenter, 3-substituted cis- and trans-prolines, and alpha-amino acid derivatives.
authors.affiliation: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Gotoh
authors.forename: Daichi
authors.initials: D
authors.lastname: Okamura
authors.forename: Hayato
authors.initials: H
authors.lastname: Ishikawa
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D004987:Ethers; C529940:diphenylprolinol silyl ether; D011392:Proline