A general, scalable, organocatalytic nitro-Michael addition to enones: enantioselective access to all-carbon quaternary stereocenters

Organic Letters
Xiaodong GuJinxing Ye

Abstract

A tert-leucine-derived chiral diamine catalyzes the asymmetric Michael addition of nitromethane to five-, six-, and seven-membered β-substituted cyclic enones with excellent enantioselectivity, offering scalable, asymmetric access to all-carbon quaternary stereocenters. The reaction scope can be expanded to include linear acyclic enones, and excellent levels of enantioselectivity are also observed. Furthermore, this organocatalytic, asymmetric nitro-Michael reaction is amenable to multigram scale-up and applications in the construction of an eudesmane sesquiterpenoid skeleton.

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Citations

Jul 8, 2016·The Journal of Organic Chemistry·Atsushi UedaMasakazu Tanaka
Feb 19, 2016·Angewandte Chemie·Lian-Dong GuoPei-Qiang Huang
Aug 8, 2015·Chemical Communications : Chem Comm·Amol P JadhavRavi P Singh
Jun 13, 2017·The Journal of Organic Chemistry·Masahiro KawadaTsuyoshi Miura
Jun 1, 2018·Organic & Biomolecular Chemistry·Agnieszka CholewiakPiotr Kwiatkowski

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