Molybdenum-mediated deconjugation of α,β-unsaturated fused-cyclopentenone phosphonates

Dorit Moradov; Abraham Rubinstein; Dmitri Gelman; Morris Srebnik

doi:10.1055/s-0031-1289751

Molybdenum-mediated deconjugation of α,β-unsaturated fused-cyclopentenone phosphonates

Dorit Moradov, Abraham Rubinstein, Dmitri Gelman, Morris Srebnik

The Hebrew University of Jerusalem

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

Abstract

The synthesis of diethyl (3-alkyl-5-oxo-4,5,6,6a-tetrahydro-1H- cyclopenta[c]furan-4-yl)phosphonates from the corresponding 3-allyloxy-1- propynylphosphonates is described. The in situ reaction involves two steps: an intramolecular Pauson-Khand reaction followed by an unusual double bond deconjugation mediated by molybdenum hexacarbonyl in dimethyl sulfoxide.

Original language	English
Pages (from-to)	1258-1262
Number of pages	5
Journal	Synthesis
Volume	44
Issue number	8
DOIs	https://doi.org/10.1055/s-0031-1289751
State	Published - 2012

Keywords

Pauson-Khand reaction
deconjugation
double bond isomerization
molybdenum
phosphonate

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1055/s-0031-1289751

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title = "Molybdenum-mediated deconjugation of α,β-unsaturated fused-cyclopentenone phosphonates",

abstract = "The synthesis of diethyl (3-alkyl-5-oxo-4,5,6,6a-tetrahydro-1H- cyclopenta[c]furan-4-yl)phosphonates from the corresponding 3-allyloxy-1- propynylphosphonates is described. The in situ reaction involves two steps: an intramolecular Pauson-Khand reaction followed by an unusual double bond deconjugation mediated by molybdenum hexacarbonyl in dimethyl sulfoxide.",

keywords = "Pauson-Khand reaction, deconjugation, double bond isomerization, molybdenum, phosphonate",

author = "Dorit Moradov and Abraham Rubinstein and Dmitri Gelman and Morris Srebnik",

year = "2012",

doi = "10.1055/s-0031-1289751",

language = "الإنجليزيّة",

volume = "44",

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journal = "Synthesis",

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TY - JOUR

T1 - Molybdenum-mediated deconjugation of α,β-unsaturated fused-cyclopentenone phosphonates

AU - Moradov, Dorit

AU - Rubinstein, Abraham

AU - Gelman, Dmitri

AU - Srebnik, Morris

PY - 2012

Y1 - 2012

N2 - The synthesis of diethyl (3-alkyl-5-oxo-4,5,6,6a-tetrahydro-1H- cyclopenta[c]furan-4-yl)phosphonates from the corresponding 3-allyloxy-1- propynylphosphonates is described. The in situ reaction involves two steps: an intramolecular Pauson-Khand reaction followed by an unusual double bond deconjugation mediated by molybdenum hexacarbonyl in dimethyl sulfoxide.

AB - The synthesis of diethyl (3-alkyl-5-oxo-4,5,6,6a-tetrahydro-1H- cyclopenta[c]furan-4-yl)phosphonates from the corresponding 3-allyloxy-1- propynylphosphonates is described. The in situ reaction involves two steps: an intramolecular Pauson-Khand reaction followed by an unusual double bond deconjugation mediated by molybdenum hexacarbonyl in dimethyl sulfoxide.

KW - Pauson-Khand reaction

KW - deconjugation

KW - double bond isomerization

KW - molybdenum

KW - phosphonate

UR - http://www.scopus.com/inward/record.url?scp=84859602926&partnerID=8YFLogxK

U2 - 10.1055/s-0031-1289751

DO - 10.1055/s-0031-1289751

M3 - مقالة

SN - 0039-7881

VL - 44

SP - 1258

EP - 1262

JO - Synthesis

JF - Synthesis

IS - 8

ER -

Molybdenum-mediated deconjugation of α,β-unsaturated fused-cyclopentenone phosphonates

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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