Catalyst- and Base-Free Synthesis of Morita-Baylis-Hillman and Rauhut-Currier Adducts of ?-Aminonitroalkenes

A facile, base-and catalyst-free synthesis of Morita???Baylis???Hillman and Rauhut???Currier adducts of fi-aminonitroalkenes with different electrophiles such as ethyl glyoxylate, trifluoropyruvate, ninhydrin, vinyl sulfone, and N-tosylazadiene is reported. The products are formed in good to excellent yields at room temperature with a broad substrate scope. The adducts of ninhydrin and fi-aminonitroalkene spontaneously cyclize to fused indenopyrroles. Gram-scale reactions and synthetic transformations of the adducts are also reported here.

Automated summary

A facile, base-and catalyst-free synthesis of Morita-Baylis-Hillman and Rauhut-Currier adducts of fi-aminonitroalkenes with different electrophiles is reported. The reactions with ethyl glyoxylate, trifluoropyruvate, ninhydrin, vinyl sulfone, and N-tosylazadiene result in good to excellent yields of products at room temperature. The adducts of ninhydrin and fi-aminonitroalkene spontaneously cyclize to fused indenopyrroles. Gram-scale reactions and synthetic transformations of the adducts are also reported.