Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium‐Catalyzed [2+2+2] Cycloaddition |
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| Authors: | Koji Masutomi Haruki Sugiyama Hidehiro Uekusa Yu Shibata Ken Tanaka |
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| Institution: | 1. http://www.apc.titech.ac.jp/～ktanaka/;2. Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan;3. Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan |
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| 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. |
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| Keywords: | asymmetric catalysis cycloadditions enamides reaction mechanisms rhodium |
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