A New Procedure for the One-Carbon Homologation of Ketones to α-Hydroxy Aldehydes

Maciej Adamczyk, E. Kurt Dolence, David Watt, M. Robert Christy, Joseph H. Reibenspies, Oren P. Anderson

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

A new, one-carbon homologation procedure for the conversion of ketones to-hydroxy aldehydes involves two steps: (1) Darzens condensation of ketones with chloromethyl phenyl sulfone; (2) ring opening of the intermediate α,β-epoxy sulfones with hydroxide ion generated by adding water to potassium tert-butoxide. This new sequence proceeds in good overall yields and with high stereoselectivity.

Original languageEnglish
Pages (from-to)1378-1382
Number of pages5
JournalJournal of Organic Chemistry
Volume49
Issue number8
DOIs
StatePublished - Nov 1984

ASJC Scopus subject areas

  • Organic Chemistry

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