Alkylidenesilacyclopropanes derived from allenes

Applications to the selective synthesis of triols and homoallylic alcohols

Kay M. Buchner, Timothy B. Clark, Janice M N Loy, Thong X. Nguyen, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.

Original languageEnglish (US)
Pages (from-to)2173-2175
Number of pages3
JournalOrganic Letters
Volume11
Issue number10
DOIs
StatePublished - May 21 2009

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triols
alcohols
Alcohols
flasks
synthesis
insertion
Regioselectivity
silver
Silver
propadiene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Alkylidenesilacyclopropanes derived from allenes : Applications to the selective synthesis of triols and homoallylic alcohols. / Buchner, Kay M.; Clark, Timothy B.; Loy, Janice M N; Nguyen, Thong X.; Woerpel, Keith.

In: Organic Letters, Vol. 11, No. 10, 21.05.2009, p. 2173-2175.

Research output: Contribution to journalArticle

Buchner, Kay M. ; Clark, Timothy B. ; Loy, Janice M N ; Nguyen, Thong X. ; Woerpel, Keith. / Alkylidenesilacyclopropanes derived from allenes : Applications to the selective synthesis of triols and homoallylic alcohols. In: Organic Letters. 2009 ; Vol. 11, No. 10. pp. 2173-2175.
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