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DOI: 10.1055/s-0029-1219840
From Vinylogation to Alkynylogation: Extending the Reactivity of Enolates
Publication History
Publication Date:
20 April 2010 (online)
Abstract
Extending reactivity through conjugated multiple carbon-carbon bonds can be a rapid way to expand the scope of synthetic chemistry. In this account, we describe our research on the alkynylogation of enolates. We conducted a systematic investigation on reactions of alkynyl- and allenyl-substituted enolates with various electrophiles. Those reactions led to the convenient synthesis of highly functionalized allenes, alkynes, and 1,3-dienes. Some relevant literature reports are also described.
1 New Chemistry through the Extension of a Known Reaction
2 Generation of Alkynyl- and Allenyl-Substituted Enolates
3 Chemistry of Alkynyl- and Allenyl-Substituted Enolates towards Electrophiles
3.1 Alkynylogous Aldol Reaction
3.2 Reactions of Alkynyl-Substituted Enolates with Alkyl Halides
3.3 Reactions of Alkynyl-Substituted Enolates with Electron-Deficient Alkenes
3.4 Halogenations of Alkynyl-Substituted Enolates
3.5 Reactions of Allenyl-Substituted Enolates
4 Concluding Remarks
Key words
vinylogation - alkynylogation - enolates - aldol reactions - halogenations
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