195734-90-8Relevant academic research and scientific papers
Chiral Lewis Acid-Mediated Enantioselective Pictet-Spengler Reaction of Nb-Hydroxytryptamine with Aldehydes
Yamada, Hideki,Kawate, Tomohiko,Matsumizu, Miyako,Nishida, Atsushi,Yamaguchi, Kentaro,Nakagawa, Masako
, p. 6348 - 6354 (1998)
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 Nb-hydroxytryptamine with aldehydes gave the corresponding 2-hydroxytetrahydro-β-carbolines in up to 90% ee. The enantioselective Pictet-Spengler reaction catalyzed by chiral binaphthol-derived Br?nsted acid-assisted Lewis acids, with up to 91% ee, is also demonstrated.
