Premium
Rhodium‐Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides
Author(s) -
Yoshida Tomoka,
Tajima Yuki,
Kobayashi Masayuki,
Masutomi Koji,
Noguchi Keiichi,
Tanaka Ken
Publication year - 2015
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.201502505
Subject(s) - rhodium , cyclopropane , cationic polymerization , cycloaddition , chemistry , enantioselective synthesis , binap , medicinal chemistry , cleavage (geology) , stereochemistry , catalysis , organic chemistry , ring (chemistry) , materials science , fracture (geology) , composite material
It has been established that a cationic rhodium(I)/H 8 ‐binap complex catalyzes the [3+2+2] cycloaddition of 1,6‐diynes with cyclopropylideneacetamides to produce cycloheptadiene derivatives through cleavage of cyclopropane rings. In contrast, a cationic rhodium(I)/( S )‐binap complex catalyzes the enantioselective [2+2+2] cycloaddition of terminal alkynes, acetylenedicarboxylates, and cyclopropylideneacetamides to produce spiro‐cyclohexadiene derivatives which retain the cyclopropane rings.