Tetrahedron

Synthesis of tetrahydroisoquinolines and isochromans via Pictet–Spengler reactions catalyzed by Brønsted acid–surfactant-combined catalyst in aqueous media

…, M Takayama, A Yamazaki, J Numaguchi, Y Hanzawa

Index: Saito, Akio; Takayama, Masaki; Yamazaki, Aru; Numaguchi, Junko; Hanzawa, Yuji Tetrahedron, 2007 , vol. 63, # 19 p. 4039 - 4047

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Citation Number: 34

Abstract

Perfluorooctanesulfonic acid (PFOSA), Brønsted acid–surfactant-combined catalyst, efficiently catalyzes the Pictet–Spengler reactions of β-arylethyl carbamate derivatives with aldehydes in water. The present reaction is accelerated by the addition of 1, 1, 1, 3, 3, 3- hexafluoro-2-propanol (HFIP). PFOSA in HFIP–water (10v/v%) is also successfully applied to the oxa-Pictet–Spengler reactions of β-arylethyl alcohol compounds.