Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe2)3-mediated tandem reaction

Sunewang Rixin Wang; Alexander T. Radosevich

doi:10.1021/ol400576e

Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe₂)₃-mediated tandem reaction

Sunewang Rixin Wang
, Alexander T. Radosevich^*

^*Corresponding author for this work

Pennsylvania State University

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

48 Scopus citations

Abstract

A reductive homocondensation of E-benzylidenepyruvate esters mediated by P(NMe₂)₃ is described. The transformation, initiated by the Kukhtin-Ramirez addition of the phosphorus reagent to the vinyl-substituted α-dicarbonyl substrate, proceeds via a resonance delocalized oxyphosphonium dienolate intermediate to provide access to diverse oxygenated heterocycles as a function of the substituent.

Original language	English
Pages (from-to)	1926-1929
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1021/ol400576e
State	Published - 19 Apr 2013
Externally published	Yes

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title = "Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe2)3-mediated tandem reaction",

abstract = "A reductive homocondensation of E-benzylidenepyruvate esters mediated by P(NMe2)3 is described. The transformation, initiated by the Kukhtin-Ramirez addition of the phosphorus reagent to the vinyl-substituted α-dicarbonyl substrate, proceeds via a resonance delocalized oxyphosphonium dienolate intermediate to provide access to diverse oxygenated heterocycles as a function of the substituent.",

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doi = "10.1021/ol400576e",

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T1 - Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe2)3-mediated tandem reaction

AU - Wang, Sunewang Rixin

AU - Radosevich, Alexander T.

PY - 2013/4/19

Y1 - 2013/4/19

N2 - A reductive homocondensation of E-benzylidenepyruvate esters mediated by P(NMe2)3 is described. The transformation, initiated by the Kukhtin-Ramirez addition of the phosphorus reagent to the vinyl-substituted α-dicarbonyl substrate, proceeds via a resonance delocalized oxyphosphonium dienolate intermediate to provide access to diverse oxygenated heterocycles as a function of the substituent.

AB - A reductive homocondensation of E-benzylidenepyruvate esters mediated by P(NMe2)3 is described. The transformation, initiated by the Kukhtin-Ramirez addition of the phosphorus reagent to the vinyl-substituted α-dicarbonyl substrate, proceeds via a resonance delocalized oxyphosphonium dienolate intermediate to provide access to diverse oxygenated heterocycles as a function of the substituent.

UR - https://www.scopus.com/pages/publications/84876536756

U2 - 10.1021/ol400576e

DO - 10.1021/ol400576e

M3 - 文章

AN - SCOPUS:84876536756

SN - 1523-7060

VL - 15

SP - 1926

EP - 1929

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe₂)₃-mediated tandem reaction

Abstract

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