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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
Author(s) -
Weng Jiang,
Li JunMing,
Li FengQuan,
Xie ZhiSheng,
Lu Gui
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200093
Subject(s) - chemistry , domino , nitro , michael reaction , neuraminidase , annulation , neuraminidase inhibitor , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , enzyme , medicine , alkyl , disease , covid-19 , infectious disease (medical specialty)
An 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.