Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides

Jude N. Arokianathar, Will Hartley, Calum McLaughlin, Mark David Greenhalgh, Darren Stead, Sean Ng, Alexandra Martha Zoya Slawin, Andrew David Smith

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3 Citations (Scopus)
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Abstract

The isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides is reported. para-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, is proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products can be isolated, or derivatized in situ by addition of benzylamine to give amides, in up to 99% yield. Although low diastereocontrol is observed, the diastereoisomeric ester products are separable and formed with high enantiocontrol (up to 94:6 er).
Original languageEnglish
Article number6333
Number of pages13
JournalMolecules
Volume26
Issue number21
DOIs
Publication statusPublished - 20 Oct 2021

Keywords

  • Isothiourea
  • Ammonium enolate
  • Ayloxide
  • Quinone methide
  • Ester functionalization
  • 1,6-conjugate addition

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