Tetrahedron Letters

Chemo-and diastereoselective Bi (OTf) 3-catalyzed benzylation of silyl nucleophiles

P Rubenbauer, T Bach

Index: Rubenbauer, Philipp; Bach, Thorsten Tetrahedron Letters, 2008 , vol. 49, # 8 p. 1305 - 1309

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Citation Number: 29

Abstract

The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi (OTf) 3 in CH3NO2 as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1–2.5 mol% of the catalyst. Benzylic acetates other than para- methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities ...