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Direct Mannich and Nitro‐Mannich Reactions with Non‐Activated Imines: AgOTf‐Catalyzed Addition of Pronucleophiles to ortho ‐Alkynylaryl Aldimines Leading to 1,2‐Dihydroisoquinolines
Author(s) -
Asao Naoki,
Yudha S. Salprima,
Nogami Tsutomu,
Yamamoto Yoshinori
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500795
Subject(s) - aldimine , protonation , nitro , catalysis , chemistry , stoichiometry , medicinal chemistry , combinatorial chemistry , organic chemistry , ion , alkyl
A variety of 1,2‐dihydroisoquinoline derivatives 3 have been prepared in good to high yields by the AgOTf‐catalyzed reaction of ortho ‐alkynylaryl aldimines 1 with various pronucleophiles 2 (see scheme). Treatment of 1 with a stoichiometric amount of AgOTf followed by protonation with TfOH produced 4 , which suggests the formation of an isoquinolinium intermediate in the present direct addition reaction. Tf=trifluoromethanesulfonyl.