Enhancement of Enantioselectivity by THF in Asymmetric Mo-Catalyzed Olefin Metathesis. Catalytic Enantioselective Synthesis of Cyclic Tertiary Ethers and Spirocycles
- 17 August 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (36) , 10779-10784
- https://doi.org/10.1021/ja020671s
Abstract
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.Keywords
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