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Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxa- and Azabicyclic Alkenes

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posted on 2007-02-14, 00:00 authored by Takahiro Nishimura, Takahiro Kawamoto, Keigo Sasaki, Eiji Tsurumaki, Tamio Hayashi
Asymmetric homo-cyclodimerization of oxabicyclic alkenes proceeded with high efficiency in the presence of a cationic rhodium/(R)-binap catalyst to give high yields of chiral tetrahydrofurans of up to 99% ee. The cationic rhodium complex also catalyzed the asymmetric cross-cyclodimerization between oxabicyclic alkenes and dimethyl 2-butynedioate, which gave dihydrofurans as [3 + 2] cycloadducts with high enantioselectivity (99% ee).

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