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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10.1016/0040-4039(92)88045-7

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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",

doi = "10.1016/0040-4039(92)88045-7",

language = "English (US)",

volume = "33",

pages = "185--188",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "2",

}

TY - JOUR

T1 - Ambiphilic allenyl enolates

T2 - reactions with electrophiles

AU - Lee, Sang Ho

AU - Shih, Mei Jue

AU - Hulce, Martin

PY - 1992

Y1 - 1992

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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U2 - 10.1016/0040-4039(92)88045-7

DO - 10.1016/0040-4039(92)88045-7

M3 - Article

AN - SCOPUS:0026512560

VL - 33

SP - 185

EP - 188

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 2

ER -

Ambiphilic allenyl enolates: reactions with electrophiles

Abstract

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