Morita-Baylis-Hillman cyclizations of arene-ruthenium-functionalized acrylamides

F. Christopher Pigge; R. Dhanya; Erik R. Hoefgen

doi:10.1002/anie.200605045

Morita-Baylis-Hillman cyclizations of arene-ruthenium-functionalized acrylamides

F. Christopher Pigge
, R. Dhanya
, Erik R. Hoefgen

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

51 Scopus citations

Abstract

Enticed by metalation with a {CpRu^II} fragment, N-benzyl and N-phenethyl acrylamides participate in phosphine-promoted spirocyclizations even though they are normally unreactive in Morita-Baylis-Hillman (MBH)-type transformations. A ruthenium-arene cation serves as the electrophilic reaction partner for an in situ generated enolate ion in this organometallic variation of the MBH reaction. (Chemical Equation Presented).

Original language	English
Pages (from-to)	2887-2890
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	16
DOIs	https://doi.org/10.1002/anie.200605045
State	Published - 2007

Keywords

Arene ligands
Dearomatization
Nitrogen heterocycles
Ruthenium
Spiro compounds

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title = "Morita-Baylis-Hillman cyclizations of arene-ruthenium-functionalized acrylamides",

abstract = "Enticed by metalation with a \{CpRuII\} fragment, N-benzyl and N-phenethyl acrylamides participate in phosphine-promoted spirocyclizations even though they are normally unreactive in Morita-Baylis-Hillman (MBH)-type transformations. A ruthenium-arene cation serves as the electrophilic reaction partner for an in situ generated enolate ion in this organometallic variation of the MBH reaction. (Chemical Equation Presented).",

keywords = "Arene ligands, Dearomatization, Nitrogen heterocycles, Ruthenium, Spiro compounds",

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pages = "2887--2890",

journal = "Angewandte Chemie - International Edition",

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T1 - Morita-Baylis-Hillman cyclizations of arene-ruthenium-functionalized acrylamides

AU - Pigge, F. Christopher

AU - Dhanya, R.

AU - Hoefgen, Erik R.

PY - 2007

Y1 - 2007

N2 - Enticed by metalation with a {CpRuII} fragment, N-benzyl and N-phenethyl acrylamides participate in phosphine-promoted spirocyclizations even though they are normally unreactive in Morita-Baylis-Hillman (MBH)-type transformations. A ruthenium-arene cation serves as the electrophilic reaction partner for an in situ generated enolate ion in this organometallic variation of the MBH reaction. (Chemical Equation Presented).

AB - Enticed by metalation with a {CpRuII} fragment, N-benzyl and N-phenethyl acrylamides participate in phosphine-promoted spirocyclizations even though they are normally unreactive in Morita-Baylis-Hillman (MBH)-type transformations. A ruthenium-arene cation serves as the electrophilic reaction partner for an in situ generated enolate ion in this organometallic variation of the MBH reaction. (Chemical Equation Presented).

KW - Arene ligands

KW - Dearomatization

KW - Nitrogen heterocycles

KW - Ruthenium

KW - Spiro compounds

UR - https://www.scopus.com/pages/publications/34250845832

U2 - 10.1002/anie.200605045

DO - 10.1002/anie.200605045

M3 - Article

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AN - SCOPUS:34250845832

SN - 1433-7851

VL - 46

SP - 2887

EP - 2890

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 16

ER -

Morita-Baylis-Hillman cyclizations of arene-ruthenium-functionalized acrylamides

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Keywords

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