Journal of Organometallic Chemistry

Reactivity of γ-benzyloxyallyltins with cyclohexylidene glyceraldehydes

F Fliegel, I Beaudet, JP Quintard

Index: Fliegel, Florian; Beaudet, Isabelle; Quintard, Jean-Paul Journal of Organometallic Chemistry, 2001 , vol. 624, # 1-2 p. 383 - 387

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Abstract

Benzyloxyallyltributyltins were obtained in 50–80% yield by SN2′ reaction of alkyl- cyanocuprates with 3, 3-dibenzyloxy-1-tributylstannylprop-1-ene in the presence of boron trifluoride. They reacted with cyclohexylidene glyceraldehyde in the presence of different Lewis acids and the obtained diastereomeric adducts were unambiguously identified after an ozonolysis/deprotection sequence by comparison with authentic aldopentoses. The ...

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