Catalyst-controlled divergent addition reactions of enoldiazoacetamides with nitrones have been developed. By using copper(I) tetrafluoroborate/bisoxazoline complex as the catalyst, a [3+3]-cycloaddition reaction was achieved with excellent yield and enantioselectivity under exceptionally mild conditions, which represents the first base metal-catalyzed asymmetric vinylcarbene transformation. When the catalyst was changed to copper(I) triflate, Mannich addition products were formed in high yields under otherwise identical conditions. Additionally, this study furnishes the first example of intermolecular reaction with vinyldiazoacetamides.

Copper-catalyzed divergent addition reactions of enoldiazoacetamides with nitrones

251st National Meeting (2016)

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