Chiral Lewis Acid-Mediated Enantioselective Pictet-Spengler Reaction of N(b)-Hydroxytryptamine with Aldehydes.
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.
Yamada
Hideki
H
Faculty of Pharmaceutical Sciences and Chemical Analytical Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan.
Kawate
Tomohiko
T
Matsumizu
Miyako
M
Nishida
Atsushi
A
Yamaguchi
Kentaro
K
Nakagawa
Masako
M