Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations

David Madec; Guillaume Prestat; Elisabetta Martini; Peter Fristrup; Giovanni Poli; Per-Ola Norrby

doi:10.1021/ol047548l

Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations

David Madec, Guillaume Prestat, Elisabetta Martini, Peter Fristrup, Giovanni Poli, Per-Ola Norrby

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS.

Original language	English
Journal	Organic Letters
Volume	7
Issue number	6
Pages (from-to)	995-998
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol047548l
Publication status	Published - 2005

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title = "Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations",

abstract = "Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS. ",

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journal = "Organic Letters",

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T1 - Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations

AU - Madec, David

AU - Prestat, Guillaume

AU - Martini, Elisabetta

AU - Fristrup, Peter

AU - Poli, Giovanni

AU - Norrby, Per-Ola

PY - 2005

Y1 - 2005

N2 - Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS.

AB - Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS.

U2 - 10.1021/ol047548l

DO - 10.1021/ol047548l

M3 - Journal article

SN - 1523-7060

VL - 7

SP - 995

EP - 998

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Surprisingly Mild Enolate-Counterion-Free Pd(0)-Catalyzed Intramolecular Allylic Alkylations

Abstract

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