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Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium‐Catalyzed [2+2+2] Cycloaddition
Author(s) -
Masutomi Koji,
Sugiyama Haruki,
Uekusa Hidehiro,
Shibata Yu,
Tanaka Ken
Publication year - 2016
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.201608952
Subject(s) - cycloaddition , enantioselective synthesis , rhodium , chemistry , regioselectivity , moiety , cationic polymerization , phosphine , amide , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
It has been established that cationic rhodium(I)/axially chiral biaryl bis(phosphine) complexes catalyze the asymmetric [2+2+2] cycloaddition of 1,6‐enynes with electron‐rich functionalized alkenes, enamides, and vinyl carboxylates, to produce the corresponding protected cyclohexenylamines and cyclohexenols. Interestingly, regioselectivity depends on structures of substrates. The present cycloaddition was successfully applied to the enantioselective total synthesis of (−)‐porosadienone by using the amide moiety as a leaving group.