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Synlett 1998; 1998(8): 903-905
DOI: 10.1055/s-1998-1804
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Kinetic Diastereoselection of Homoallylic Indium Alkoxides: Syn Crotylation of Arylaldehydes

Guy C. Lloyd-Jones* , Tim Russell
  • *School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK; Fax + 44(117)929 8611; E-mail: guy.lloyd-jones@bristol.ac.uk
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Publication Date:
31 December 2000 (online)

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Reaction of crotylindium sesquibromide with benzaldehyde in DMF at 20 °C affords syn-1-phenyl-2-methylbut-3-enol (ca. 40% de) after aqueous acidic work-up. At 22 °C in DMF, prior to work-up a greater relative proportion of the anti intermediate is decomposed as compared to its syn diastereomer. The resultant kinetic diastereoselection upgrades, the syn/anti ratio to 99/1 with a concomitant drop in overall yield.

indium - allyl - kinetic diastereoselection - crotyl - aldehyde