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Synthesis 1993; 1993(11): 1133-1140
DOI: 10.1055/s-1993-26015
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Palladium(0)-Catalysed Hydrostannylation of 1-Alkoxy-1-alkynes: A Synthesis of α-Alkoxyalkenylstannanes and Their Transmetallation to α-Alkoxyalkenyllithiums

Sharon Casson* , Philip Kocieński
  • *Department of Chemistry, The University, Southampton, SO9 5NH, England
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Publication Date:
29 April 2002 (online)

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1-Alkoxy-1-alkynes undergo rapid hydrostannylation with trialkylstannanes in the presence of catalytic amounts of palladium(0). The reaction gives clean cis-addition with the tin being placed preferentially in the α-position The resultant α-alkoxyalkenylstannanes transmetallate efficiently with BuLi to α-alkoxyalkenyllithiums which were previously accessible only with difficulty.