Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution |
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| Authors: | Shunsuke Suzuki Dr Yu Shibata Prof Dr Ken Tanaka |
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| Institution: | Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550 Japan |
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| Abstract: | It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asymmetric 2+2+2] cycloaddition of 1,6-enynes with racemic secondary allylic alcohols to produce the corresponding chiral bicyclic cyclohexenes, possessing three stereogenic centers, as a single diastereomer with excellent ee values. Mechanistic experiments revealed that the present cycloaddition proceeds through the kinetic resolution of the racemic secondary allylic alcohols, in which one enantiomer preferentially reacts with the 1,6-enyne. |
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| Keywords: | allylic alcohols asymmetric [2+2+2] cycloaddition enynes kinetic resolution rhodium |
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