HELVETICA CHIMICA ACTA, cilt.104, sa.12, 2021 (SCI-Expanded)
The B,N-bifunctional catalyst homoboroproline has been applied to a catalytic asymmetric nitroalkene-Michael addition to beta-nitrostyrene analogues, showing broad substrate tolerance, high conversions and moderate to good asymmetric induction. The ability of homoboroproline to act as an efficient catalyst based on enamine-formation of the secondary amine, coupled with intramolecular Lewis-acid chelation of the nitro function, in a non-FLP manner, to effect efficient and enantioselective catalysis via a proposed large 10-membered ring transition state is remarkable and reinforced by theoretical calculations.