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

doi:10.1016/S0040-4020(98)00006-4

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

Fundamental Organic Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	2411-2422
Number of pages	12
Journal	Tetrahedron
Volume	54
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(98)00006-4
Publication status	Published - 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

Shindo, M., Sato, Y., & Shishido, K. (1998). Novel synthesis of ynolates via the cleavage of ester dianions: α-bromo and α,α-dibromo esters as precursors. Tetrahedron, 54(11), 2411-2422. https://doi.org/10.1016/S0040-4020(98)00006-4

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 journal › Article

Shindo, M, Sato, Y & Shishido, K 1998, 'Novel synthesis of ynolates via the cleavage of ester dianions: α-bromo and α,α-dibromo esters as precursors', Tetrahedron, vol. 54, no. 11, pp. 2411-2422. https://doi.org/10.1016/S0040-4020(98)00006-4

Shindo M, Sato Y, Shishido K. Novel synthesis of ynolates via the cleavage of ester dianions: α-bromo and α,α-dibromo esters as precursors. Tetrahedron. 1998 Mar 12;54(11):2411-2422. https://doi.org/10.1016/S0040-4020(98)00006-4

Shindo, Mitsuru ; Sato, Yusuke ; Shishido, Kozo. / Novel synthesis of ynolates via the cleavage of ester dianions : α-bromo and α,α-dibromo esters as precursors. In: Tetrahedron. 1998 ; Vol. 54, No. 11. pp. 2411-2422.

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10.1016/S0040-4020(98)00006-4