Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes

Jared T. Shaw, K. A. Woerpel

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The insertion of formamides into a C-Si bond of silirane trans- 1 provides a facile route to the oxasilacyclopentane acetate 5 (86% overall yield). Stereoselective carbon-carbon bond formation on the derived oxonium ion was achieved by addition of the silyl enol ether of acetophenone (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis.

Original languageEnglish (US)
Pages (from-to)16597-16606
Number of pages10
JournalTetrahedron
Volume53
Issue number48
DOIs
StatePublished - Dec 1 1997

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Acetals
Formamides
Carbon
Pentanones
Synthetic Chemistry Techniques
Ether
Acetates
Ions
hydronium ion
acetophenone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes. / Shaw, Jared T.; Woerpel, K. A.

In: Tetrahedron, Vol. 53, No. 48, 01.12.1997, p. 16597-16606.

Research output: Contribution to journalArticle

Shaw, Jared T. ; Woerpel, K. A. / Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes. In: Tetrahedron. 1997 ; Vol. 53, No. 48. pp. 16597-16606.
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