PALLADIUM(0)-CATALYZED HYDROSTANNYLATION OF 1-ALKOXY-1-ALKYNES - A SYNTHESIS OF ALPHA-ALKOXY-ALKENYLSTANNANES AND THEIR TRANSMETALATION TO ALPHA-ALKOXYALKENYLLITHIUMS

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 alpha-position. The resultant alpha-alkoxyalkenylstannanes transmetallate efficiently...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 11; pp. 1133 - 1140
Main Authors CASSON, S, KOCIENSKI, P
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
HYDROSTANNATION
ACETYLENES
ETHERS
CATALYZED REACTIONS
VINYLSTANNANES
ORGANIC HALIDES
ALKYNES
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Summary: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 alpha-position. The resultant alpha-alkoxyalkenylstannanes transmetallate efficiently with BuLi to alpha-alkoxyalkenyllithiums which were previously accessible only with difficulty.
ISSN:0039-7881