Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds

A RhI/(S)-BINAP catalytic system is able to promote carbene alkyne metathesis and cascade this elemental step with an stereoselective reaction with allenes. An unusual carbene/allene reactivity is discovered that, through a formal addition of p-toluenesulfinic acid to a Rh-bound trimethylenemethane intermediate, affords 4-methylenetetrahydropyran compounds in good yields and excellent enantioselectivities ​
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