Radical addition reactions of chiral phosphorus hydrides

C M  Jessop; A F  Parsons; A  Routledge; D J  Irvine

doi:10.1016/j.tetasy.2003.04.001

Radical addition reactions of chiral phosphorus hydrides

C M Jessop, A F Parsons, A Routledge, D J Irvine

Chemistry

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

Abstract

Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2849-2851
Number of pages	3
Journal	TETRAHEDRON-ASYMMETRY
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.tetasy.2003.04.001
Publication status	Published - 3 Oct 2003

Keywords

ASYMMETRIC-SYNTHESIS
EFFICIENT SYNTHESIS
BORONIC ESTERS
PHOSPHONOTHIOATES
PHOSPHONATES
ALKENES

Access to Document

10.1016/j.tetasy.2003.04.001

Cite this

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title = "Radical addition reactions of chiral phosphorus hydrides",

abstract = "Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "ASYMMETRIC-SYNTHESIS, EFFICIENT SYNTHESIS, BORONIC ESTERS, PHOSPHONOTHIOATES, PHOSPHONATES, ALKENES",

author = "Jessop, {C M} and Parsons, {A F} and A Routledge and Irvine, {D J}",

year = "2003",

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doi = "10.1016/j.tetasy.2003.04.001",

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journal = "TETRAHEDRON-ASYMMETRY",

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TY - JOUR

T1 - Radical addition reactions of chiral phosphorus hydrides

AU - Jessop, C M

AU - Parsons, A F

AU - Routledge, A

AU - Irvine, D J

PY - 2003/10/3

Y1 - 2003/10/3

N2 - Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.

KW - ASYMMETRIC-SYNTHESIS

KW - EFFICIENT SYNTHESIS

KW - BORONIC ESTERS

KW - PHOSPHONOTHIOATES

KW - PHOSPHONATES

KW - ALKENES

U2 - 10.1016/j.tetasy.2003.04.001

DO - 10.1016/j.tetasy.2003.04.001

M3 - Article

SN - 0957-4166

VL - 14

SP - 2849

EP - 2851

JO - TETRAHEDRON-ASYMMETRY

JF - TETRAHEDRON-ASYMMETRY

IS - 19

ER -