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Triflic Acid Catalyzed Synthesis of Spirocycles via Acetylene Cations
Author(s) -
Jin Tienan,
Himuro Masafumi,
Yamamoto Yoshinori
Publication year - 2009
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.200901771
Subject(s) - triflic acid , acetylene , yield (engineering) , chemistry , catalysis , stereoselectivity , bicyclic molecule , ring (chemistry) , organic chemistry , combinatorial chemistry , materials science , metallurgy
Rings of various shapes and sizes : Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl‐substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.