title: One-pot construction of multiple contiguous chiral centers using Michael addition of chiral amine.
abstract: Multiple contiguous chiral centers were constructed in one pot using three types of multistep reactions initiated with the Michael addition of N-benzyl-2(R)-methoxy-(+)-10-bornylamide to alpha,beta-unsaturated esters, i.e., asymmetric Michael-aldol reaction, double Michael addition, and double Michael-aldol reaction. The chiral 2-methoxy-10-bornyl group as well as the benzyl group on the amino group of the products in the Michael-aldol reaction could be easily cleaved by treatment with NIS (4 equiv), and beta-amino esters with multiple contiguous chiral centers were obtained in good yield. As an application, the beta-amino-beta'-hydroxy ester obtained in the asymmetric Michael-aldol reaction was converted to the beta-lactam derivative in good yield.
authors.affiliation: Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Minoru
authors.initials: M
authors.lastname: Ozeki
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Ochi
authors.forename: Noboru
authors.initials: N
authors.lastname: Hayama
authors.forename: Shinzo
authors.initials: S
authors.lastname: Hosoi
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kajimoto
authors.forename: Manabu
authors.initials: M
authors.lastname: Node
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000588:Amines; D004952:Esters