Thiol-promoted selective addition of ketones to aldehydes

Regev Parnes, Sachin Narute, Doron Pappo

Research output: Contribution to journalArticlepeer-review

Abstract

A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.

Original languageAmerican English
Pages (from-to)5922-5925
Number of pages4
JournalOrganic Letters
Volume16
Issue number22
DOIs
StatePublished - 21 Nov 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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