Asymmetric Domino Nitro‐Michael/Horner–Wadsworth–Emmons Reaction for Disubstituted Cyclohexenecarboxylate Annulation: Efficient Synthesis of Dipeptidyl Peptidase IV Inhibitor ABT‐341 and Influenza Neuraminidase Inhibitor

Abstract

AbstractAn asymmetric domino nitro‐Michael/Horner–Wadsworth–Emmons (HWE) reaction involving α,β‐unsaturated aldehydes and nitro phosphonates has been developed, which gave 4,5‐disubstituted cyclohexenecarboxylates with high stereoselectivities (dr up to >20:1, ee 83–92%) in good yields (44–76%). Furthermore, using this methodology as a key step, a short and practical synthesis of pharmaceutically useful compounds (such as the dipeptidyl peptidase IV inhibitor ABT‐341 and an influenza neuraminidase inhibitor) has also been accomplished.