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

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 i...

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Bibliographic Details
Published inTetrahedron Vol. 63; no. 19; pp. 4039 - 4047
Main Authors Saito, Akio, Takayama, Masaki, Yamazaki, Aru, Numaguchi, Junko, Hanzawa, Yuji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.05.2007
Elsevier
Subjects
Brønsted acid
Chemistry
Chemistry, Organic
Isochroman
Isoquinoline
Physical Sciences
Pictet–Spengler reaction
Science & Technology
Surfactant
Brønsted acid
Isoquinoline
Pictet–Spengler reaction
Surfactant
Isochroman
ALCOHOLS
bronsted acid
isoquinoline
MANNICH-TYPE REACTION
AMINES
ETHER
isochroman
ALDEHYDES
Pictet-Spengler reaction
DERIVATIVES
surfactant
WATER
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Summary: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 (10 v/v %) is also successfully applied to the oxa-Pictet–Spengler reactions of β-arylethyl alcohol compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.02.123