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Rhodium‐Catalyzed Cyclization Reactions of γ‐Alkynyl Aldehydes with Carboxylic Acid Anhydrides
Author(s) -
Tajima Yuki,
Kobayashi Masayuki,
Noguchi Keiichi,
Tanaka Ken
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300734
Subject(s) - chemistry , aldehyde , rhodium , allylic rearrangement , carboxylic acid , cationic polymerization , binap , medicinal chemistry , catalysis , organic chemistry , enantioselective synthesis
It has been established that a cationic rhodium(I)/H 8 ‐binap or binap complex catalyzes two different modes of cyclization of γ‐alkynyl aldehydes with carboxylic acid anhydrides to give cyclic aldehyde gem ‐dicarboxylates and cyclic alkenyl esters through cleavage of the carboxylic acid anhydride C–O bond. The reaction of a terminal γ‐alkynyl aldehyde with diethyl pyrocarbonate afforded a cyclic allylic carbonate with a high ee value.