Organic Letters
Organic Letters
5 years ago

Phosphine-Catalyzed Diastereo- and Enantioselective Michael Addition of β-Carbonyl Esters to β-Trifluoromethyl and β-Ester Enones: Enhanced Reactivity by Inorganic Base

Phosphine-Catalyzed Diastereo- and Enantioselective Michael Addition of β-Carbonyl Esters to β-Trifluoromethyl and β-Ester Enones: Enhanced Reactivity by Inorganic Base
Lu Liu, Cao Li, Huamin Wang, Ben Huang, Junliang Zhang, Caihui Wang
A novel chiral biamide–phosphine multifunctional catalyst has been developed that mediates the asymmetric intermolecular Michael addition of β-carbonyl esters to β-trifluoromethyl enones and 3-aroyl acrylates in the presence of competing methyl acrylate and the inorganic base. This method provides a facile access to structurally diverse trifluoromethyl and quaternary stereogenic centers with excellent enantioselectivity (up to 99% ee) and good diastereoselectivity (up to 13:1 dr). The addition of the inorganic base (K3PO4) does not cause the background racemic reaction and enhances the reactivity by serving as a co-catalyst.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02365

DOI: 10.1021/acs.orglett.7b02365

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