title: Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition.
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.
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Masutomi
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Haruki
authors.initials: H
authors.lastname: Sugiyama
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Yu
authors.initials: Y
authors.lastname: Shibata
authors.affiliation: Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Tanaka
keywords: asymmetric catalysis; cycloadditions; enamides; reaction mechanisms; rhodium