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Synthesis 2000; 2000(7): 990-998
DOI: 10.1055/s-2000-6303
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Diastereoselective Allylation and Crotylation Reactions of Aldehydes with Potassium Allyl- and Crotyltrifluoroborates under Lewis Acid Catalysis

Robert A. Batey* , Avinash N. Thadani, David V. Smil, Alan J. Lough
  • *Department of Chemistry, Lash Miller Laboratories, 80 St. George Street, University of Toronto, Toronto, Ontario, M5S 3H6, Canada; Fax +1(416)9785059; E-mail: rbatey@chem.utoronto.ca
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Publication Date:
31 December 2000 (online)

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Potassium allyl- and crotyltrifluoroborates react with aldehydes in a process catalyzed by a variety of Lewis acids, to give the corresponding homoallylic alcohols. Of the Lewis acids examined, BF3 · OEt2, used either stoichiometrically or catalytically, was found to most efficiently catalyze this reaction. The air and moisture stable potassium organotrifluoroborate salts react with a variety of alkyl, α- or β-substituted alkyl, and aryl aldehydes, and lead to the adducts in high yield and with high diastereoselectivity.

allylations - boron - alcohols - Lewis acids - catalysis

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