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Synlett 1998; 1998(4): 377-378
DOI: 10.1055/s-1998-1679
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Protic Solvent-Promoted Neutral Allylation of Aldehydes and Ketones with 1,8-Bis(allylstannyl)naphthalenes

Naoki Asao* , Noriko Abe, Zheng Tan, Keiji Maruoka
  • *Department of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan; Fax + 81-11-746-2557; E-mail: maruoka@sci.hokudai.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF3CH2OH (5:1) as solvent. The rate acceleration was due to the enhancement of the Brønsted acidity of CF3CH2OH by the formation of the chelate complex 6 (R = CH2CF3) resulting from the chelation effect of two neighboring tin atoms.

neutral condition - allylation - Lewis Acid - solvent effect - allylstannane