Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates

Paul M. Bodnar, Wylie S. Palmer, Brian H. Ridgway, Jared T. Shaw, Jacqueline H. Smitrovich, K. A. Woerpel

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Siliranes undergo stereoselective and regioselective insertions of benzaldehyde to provide oxasilacyclopentane products. The thermal reaction (>100°C) leads to more decomposition and side products, whereas the catalyzed variant (t-BuOK, <25°C) proceeds more cleanly with a high degree of inversion (>95%). Treatment of siliranes with enolizable aldehydes leads to silyl enol ethers. The reaction of a silirane at high temperatures with an imine leads to reductive dimerization, presumably by way of intermediate-free silylene. The mechanism for the catalyzed insertion of benzaldehyde is discussed.

Original languageEnglish (US)
Pages (from-to)4737-4745
Number of pages9
JournalJournal of Organic Chemistry
Volume62
Issue number14
StatePublished - 1997

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Stereoselectivity
Regioselectivity
Aldehydes
Imines
Ethers
Dimerization
Substrates
Decomposition
Temperature
benzaldehyde
Hot Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bodnar, P. M., Palmer, W. S., Ridgway, B. H., Shaw, J. T., Smitrovich, J. H., & Woerpel, K. A. (1997). Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates. Journal of Organic Chemistry, 62(14), 4737-4745.

Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates. / Bodnar, Paul M.; Palmer, Wylie S.; Ridgway, Brian H.; Shaw, Jared T.; Smitrovich, Jacqueline H.; Woerpel, K. A.

In: Journal of Organic Chemistry, Vol. 62, No. 14, 1997, p. 4737-4745.

Research output: Contribution to journalArticle

Bodnar, PM, Palmer, WS, Ridgway, BH, Shaw, JT, Smitrovich, JH & Woerpel, KA 1997, 'Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates', Journal of Organic Chemistry, vol. 62, no. 14, pp. 4737-4745.
Bodnar PM, Palmer WS, Ridgway BH, Shaw JT, Smitrovich JH, Woerpel KA. Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates. Journal of Organic Chemistry. 1997;62(14):4737-4745.
Bodnar, Paul M. ; Palmer, Wylie S. ; Ridgway, Brian H. ; Shaw, Jared T. ; Smitrovich, Jacqueline H. ; Woerpel, K. A. / Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 14. pp. 4737-4745.
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