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Enhancement of Enantioselectivity by THF in Asymmetric Mo-Catalyzed Olefin Metathesis. Catalytic Enantioselective Synthesis of Cyclic Tertiary Ethers and Spirocycles

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journal contribution
posted on 17.08.2002, 00:00 by Xin Teng, Dustin R. Cefalo, Richard R. Schrock, Amir H. Hoveyda
Mo-catalyzed enantioselective rearrangement of achiral cyclopentenyl tertiary ethers to chiral cyclohexenyl tertiary ethers are reported. These olefin metathesis transformations proceed efficiently and with high levels of enantioselectivity. A noteworthy feature of these reactions is that added tetrahydrofuran exerts a remarkably positive influence on the enantioselectivity of the metathesis-based rearrangement. The first examples of catalytic asymmetric synthesis of spirocyclic structures by enantioselective olefin metathesis are also disclosed.