Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with Horner-Wadsworth-Emmons-type reactions

M P  Healy; A F  Parsons; J G T  Rawlinson

doi:10.1021/ol050292e

Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with Horner-Wadsworth-Emmons-type reactions

M P Healy, A F Parsons, J G T Rawlinson

Chemistry

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

Abstract

Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.

Original language	English
Pages (from-to)	1597-1600
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	8
DOIs	https://doi.org/10.1021/ol050292e
Publication status	Published - 14 Apr 2005

Keywords

EFFICIENT METHODOLOGY
CYCLIZATION REACTIONS
COUPLING REACTIONS
CENTERED RADICALS
CHAIN-REACTIONS
HYPOPHOSPHITE
ESTERS
ACID
PHOSPHONATES
PHOSPHITES

Access to Document

10.1021/ol050292e

http://dx.doi.org/10.1021/ol050292e

Cite this

@article{1aee4eba610041c398db5ec6bbf0f958,

title = "Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with Horner-Wadsworth-Emmons-type reactions",

abstract = "Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.",

keywords = "EFFICIENT METHODOLOGY, CYCLIZATION REACTIONS, COUPLING REACTIONS, CENTERED RADICALS, CHAIN-REACTIONS, HYPOPHOSPHITE, ESTERS, ACID, PHOSPHONATES, PHOSPHITES",

author = "Healy, {M P} and Parsons, {A F} and Rawlinson, {J G T}",

year = "2005",

month = apr,

day = "14",

doi = "10.1021/ol050292e",

language = "English",

volume = "7",

pages = "1597--1600",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with Horner-Wadsworth-Emmons-type reactions

AU - Healy, M P

AU - Parsons, A F

AU - Rawlinson, J G T

PY - 2005/4/14

Y1 - 2005/4/14

N2 - Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.

AB - Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.

KW - EFFICIENT METHODOLOGY

KW - CYCLIZATION REACTIONS

KW - COUPLING REACTIONS

KW - CENTERED RADICALS

KW - CHAIN-REACTIONS

KW - HYPOPHOSPHITE

KW - ESTERS

KW - ACID

KW - PHOSPHONATES

KW - PHOSPHITES

U2 - 10.1021/ol050292e

DO - 10.1021/ol050292e

M3 - Article

SN - 1523-7060

VL - 7

SP - 1597

EP - 1600

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -