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Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

ABSTRACT: A convenient method is described for the dehydration of beta-ketoesters to generate conjugated and deconjugated alkynyl esters and conjugated allenyl esters. This sequential one-pot method involves the formation of a vinyl triflate monoanion intermediate that leads to the selective formation of alkynes or allenes depending on additives and conditions used. Product outcomes appear to be a function of unique mono- and dianion mechanisms which are described.

SUBMITTER: Maity P

PROVIDER: S-EPMC2652892 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

Maity Pradip P Lepore Salvatore D SD

The Journal of organic chemistry 20090101 1

A convenient method is described for the dehydration of beta-ketoesters to generate conjugated and deconjugated alkynyl esters and conjugated allenyl esters. This sequential one-pot method involves the formation of a vinyl triflate monoanion intermediate that leads to the selective formation of alkynes or allenes depending on additives and conditions used. Product outcomes appear to be a function of unique mono- and dianion mechanisms which are described. ...[more]

PMID: 19063594

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