A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I

Paul Knochel, Chaodong Xiao, Ming Chang P. Yeh

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The 1,1-diorganometallics of magnesium and zinc 1 are converted by the reaction with Me3SnCl to the 1,1-diorganometallics of tin and zinc 2 which are readily oxidized by dry air at -10° to 0°C to afford the corresponding aldehydes and ketones 3 in 57-91% yield. This mild oxidation reaction allows a new stereoselective approach to aldol products. An extension of the reaction to 1,1-diorganometallics of silicon and zinc is described.

Original languageEnglish
Pages (from-to)6697-6700
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number51
DOIs
Publication statusPublished - 1988

Fingerprint

Ketones
Aldehydes
Zinc
Oxidation
Tin
Silicon
Magnesium
Air
3-hydroxybutanal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A mild oxidation of 1,1-diorganometallics to ketones and aldehydes. A new stereoselective approach to aldol products part I. / Knochel, Paul; Xiao, Chaodong; Yeh, Ming Chang P.

In: Tetrahedron Letters, Vol. 29, No. 51, 1988, p. 6697-6700.

Research output: Contribution to journalArticle

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