Stereochemical and spectroscopic studies on the reaction of allylstannanes with aldehydes

Scott E. Denmark, Eric J. Weber, Thomas M. Wilson, Timothy M. Willson

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The orientational preference for the reacting double bonds in the Lewis acid-induced reaction of allylic stannanes and aldehydes has been examined. Model system 1 shows a strong and Lewis-acid independent preference for the synclinal orientation of double bonds. A possible stereoelectronic basis for this preference is discussed. A 13C-NMR spcctroscopic study of the reaction between crotyltrialkylstannanes (9) and acetaldehyde (10), pivaldehyde (11) and 4-t-butylbenzaldehyde (12) in the presence of BF3·OEt2 and SnCl4 is described. The spectroscopic study reveals that with BF3·OEt2 only direct addition occurs while with SnCl4 the pathway (addition vs. metathesis) is stoichiometry and aldehyde dependent. The mechanism of metathesis and chlorostannane isomerization is discussed.

Original languageEnglish (US)
Pages (from-to)1053-1065
Number of pages13
Issue number4
StatePublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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