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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608952
Subject(s) - cycloaddition , enantioselective synthesis , rhodium , chemistry , regioselectivity , moiety , cationic polymerization , phosphine , catalysis , amide , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
Abstract 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.