1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents

Stewart K. Richardson; Alwarsamy Jeganathan; David S. Watt

doi:10.1016/S0040-4039(00)96117-3

1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents

Stewart K. Richardson
, Alwarsamy Jeganathan
, David S. Watt

Molecular and Cellular Biochemistry

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

21 Scopus citations

Abstract

The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.

Original language	English
Pages (from-to)	2335-2338
Number of pages	4
Journal	Tetrahedron Letters
Volume	28
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)96117-3
State	Published - 1987

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents",

abstract = "The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.",

author = "Richardson, \{Stewart K.\} and Alwarsamy Jeganathan and Watt, \{David S.\}",

year = "1987",

doi = "10.1016/S0040-4039(00)96117-3",

language = "English",

volume = "28",

pages = "2335--2338",

number = "21",

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TY - JOUR

T1 - 1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes

T2 - Unsaturated homoenolate anion equivalents

AU - Richardson, Stewart K.

AU - Jeganathan, Alwarsamy

AU - Watt, David S.

PY - 1987

Y1 - 1987

N2 - The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.

AB - The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.

UR - https://www.scopus.com/pages/publications/0000207446

UR - https://www.scopus.com/pages/publications/0000207446#tab=citedBy

U2 - 10.1016/S0040-4039(00)96117-3

DO - 10.1016/S0040-4039(00)96117-3

M3 - Article

AN - SCOPUS:0000207446

SN - 0040-4039

VL - 28

SP - 2335

EP - 2338

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents

Abstract

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