Regiodivergent Asymmetric Conjugate Addition of 2-Furfuryl Ketones to Nitroalkenes Using Thiourea Organocatalysts

Abstract

We recently reported the asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes utilizing a thiourea–pyrrolidine organocatalyst, resulting in good yields and enantioselectivities. In this study, we present a novel approach for the asymmetric α-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea–tertiary amine organocatalyst, which has not been previously documented. The reactions produced α-regioselective addition products in high yields and with excellent stereoselectivities. Thus, this work marks the first example of regiodivergent asymmetric conjugate addition of 2-furfuryl ketones to nitroalkenes.

Keywords

Organocatalyst - Asymmetric - Conjugate addition - Regiodivergent reaction - 2-Furfuryl ketones - Nitroalkene

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