Novel synthesis of ynolates via the cleavage of ester dianions

α-bromo and α,α-dibromo esters as precursors

Mitsuru Shindo, Yusuke Sato, Kozo Shishido

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Ynolates have been synthesized via the thermally-induced cleavage of ester dianions. The key intermediates, ester dianions, were generated from α-bromocarboxylic acid ester enolates via lithium halogen exchange. α,α-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of tert-BuLi. The reactions of ynolates, generated by this novel and convenient method, with aldehydes to give β-lactons are discussed.

Original languageEnglish
Pages (from-to)2411-2422
Number of pages12
JournalTetrahedron
Volume54
Issue number11
DOIs
Publication statusPublished - Mar 12 1998

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Esters
Lithium
Halogens
Acids
Aldehydes
Amides

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Novel synthesis of ynolates via the cleavage of ester dianions : α-bromo and α,α-dibromo esters as precursors. / Shindo, Mitsuru; Sato, Yusuke; Shishido, Kozo.

In: Tetrahedron, Vol. 54, No. 11, 12.03.1998, p. 2411-2422.

Research output: Contribution to journalArticle

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