The use of the alkali metal dianion of methallyl alcohol in the synthesis of α-methylene-δ-valerolactones

Robert M Carlson, Linda L. White

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Recent efforts in our laboratory have focused on the generation of synthetically useful dianions in which an alkoxide is used to uniquely direct subsequent carbanion formation away 1–5 from the allylic carbon bearing the charged oxygen. The overall utility of this concept has now been extended to the synthesis of α-methylene-δ-valerolactones in which the first step is the reaction of methyllyl alcohol dianion and an epoxide (Scheme I).

Original languageEnglish (US)
Pages (from-to)237-241
Number of pages5
JournalSynthetic Communications
Volume13
Issue number3
DOIs
StatePublished - Mar 1 1983

Fingerprint

Bearings (structural)
Alkali Metals
Epoxy Compounds
Carbon
Alcohols
Oxygen

Cite this

The use of the alkali metal dianion of methallyl alcohol in the synthesis of α-methylene-δ-valerolactones. / Carlson, Robert M; White, Linda L.

In: Synthetic Communications, Vol. 13, No. 3, 01.03.1983, p. 237-241.

Research output: Contribution to journalArticle

@article{268cca0382cd48a89b0540a79f107a74,
title = "The use of the alkali metal dianion of methallyl alcohol in the synthesis of α-methylene-δ-valerolactones",
abstract = "Recent efforts in our laboratory have focused on the generation of synthetically useful dianions in which an alkoxide is used to uniquely direct subsequent carbanion formation away 1–5 from the allylic carbon bearing the charged oxygen. The overall utility of this concept has now been extended to the synthesis of α-methylene-δ-valerolactones in which the first step is the reaction of methyllyl alcohol dianion and an epoxide (Scheme I).",
author = "Carlson, {Robert M} and White, {Linda L.}",
year = "1983",
month = "3",
day = "1",
doi = "10.1080/00397918308065995",
language = "English (US)",
volume = "13",
pages = "237--241",
journal = "Synthetic Communications",
issn = "0039-7911",
publisher = "Taylor and Francis Ltd.",
number = "3",

}

TY - JOUR

T1 - The use of the alkali metal dianion of methallyl alcohol in the synthesis of α-methylene-δ-valerolactones

AU - Carlson, Robert M

AU - White, Linda L.

PY - 1983/3/1

Y1 - 1983/3/1

N2 - Recent efforts in our laboratory have focused on the generation of synthetically useful dianions in which an alkoxide is used to uniquely direct subsequent carbanion formation away 1–5 from the allylic carbon bearing the charged oxygen. The overall utility of this concept has now been extended to the synthesis of α-methylene-δ-valerolactones in which the first step is the reaction of methyllyl alcohol dianion and an epoxide (Scheme I).

AB - Recent efforts in our laboratory have focused on the generation of synthetically useful dianions in which an alkoxide is used to uniquely direct subsequent carbanion formation away 1–5 from the allylic carbon bearing the charged oxygen. The overall utility of this concept has now been extended to the synthesis of α-methylene-δ-valerolactones in which the first step is the reaction of methyllyl alcohol dianion and an epoxide (Scheme I).

UR - http://www.scopus.com/inward/record.url?scp=84948340868&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84948340868&partnerID=8YFLogxK

U2 - 10.1080/00397918308065995

DO - 10.1080/00397918308065995

M3 - Article

AN - SCOPUS:84948340868

VL - 13

SP - 237

EP - 241

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 3

ER -