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

Research output: Contribution to journal › Article › peer-review

53 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
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(98)00006-4

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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.",

author = "Mitsuru Shindo and Yusuke Sato and Kozo Shishido",

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doi = "10.1016/S0040-4020(98)00006-4",

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T1 - Novel synthesis of ynolates via the cleavage of ester dianions

T2 - α-bromo and α,α-dibromo esters as precursors

AU - Shindo, Mitsuru

AU - Sato, Yusuke

AU - Shishido, Kozo

PY - 1998/3/12

Y1 - 1998/3/12

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(98)00006-4

DO - 10.1016/S0040-4020(98)00006-4

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EP - 2422

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 11

ER -

Novel synthesis of ynolates via the cleavage of ester dianions: α-bromo and α,α-dibromo esters as precursors

Abstract

All Science Journal Classification (ASJC) codes

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