title: Chiral Lewis Acid-Mediated Enantioselective Pictet-Spengler Reaction of N(b)-Hydroxytryptamine with Aldehydes.
abstract: The first example of a reagent-controlled enantioselective Pictet-Spengler reaction is demonstrated. Using diisopinocampheylchloroborane as a chiral Lewis acid catalyst, the Pictet-Spengler reaction of N(b)-hydroxytryptamine with aldehydes gave the corresponding 2-hydroxytetrahydro-beta-carbolines in up to 90% ee. The enantioselective Pictet-Spengler reaction catalyzed by chiral binaphthol-derived Brønsted acid-assisted Lewis acids, with up to 91% ee, is also demonstrated.
authors.affiliation: Faculty of Pharmaceutical Sciences and Chemical Analytical Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Yamada
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Kawate
authors.forename: Miyako
authors.initials: M
authors.lastname: Matsumizu
authors.forename: Atsushi
authors.initials: A
authors.lastname: Nishida
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Masako
authors.initials: M
authors.lastname: Nakagawa