Ambiphilic allenyl enolates: reactions with electrophiles

Sang Ho Lee; Mei Jue Shih; Martin Hulce

doi:10.1016/0040-4039(92)88045-7

Ambiphilic allenyl enolates: reactions with electrophiles

Sang Ho Lee, Mei Jue Shih, Martin Hulce

Department of Chemistry

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

10 Scopus citations

Abstract

Allenyl enolates generated from 1,6 additions of organocopper reagents to 3-ethynyl-2-cycloalkenones act as ambident α,γ-nucleophiles. The γ:α ratio of products is a function of carbon hybridization, steric environment, and cycloalkenone ring size; typically, γ-products predominate.

Original language	English (US)
Pages (from-to)	185-188
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	2
DOIs	https://doi.org/10.1016/0040-4039(92)88045-7
State	Published - 1992

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Ambiphilic allenyl enolates: reactions with electrophiles",

abstract = "Allenyl enolates generated from 1,6 additions of organocopper reagents to 3-ethynyl-2-cycloalkenones act as ambident α,γ-nucleophiles. The γ:α ratio of products is a function of carbon hybridization, steric environment, and cycloalkenone ring size; typically, γ-products predominate.",

author = "Lee, {Sang Ho} and Shih, {Mei Jue} and Martin Hulce",

year = "1992",

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journal = "Tetrahedron Letters",

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AU - Shih, Mei Jue

AU - Hulce, Martin

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N2 - Allenyl enolates generated from 1,6 additions of organocopper reagents to 3-ethynyl-2-cycloalkenones act as ambident α,γ-nucleophiles. The γ:α ratio of products is a function of carbon hybridization, steric environment, and cycloalkenone ring size; typically, γ-products predominate.

AB - Allenyl enolates generated from 1,6 additions of organocopper reagents to 3-ethynyl-2-cycloalkenones act as ambident α,γ-nucleophiles. The γ:α ratio of products is a function of carbon hybridization, steric environment, and cycloalkenone ring size; typically, γ-products predominate.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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