Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction

E  Hevia; J  Perez; V  Riera; D  Miguel; P  Campomanes; M I  Menendez; T L  Sordo; S  Garcia-Granda

doi:10.1021/ja034070s

Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction

E Hevia, J Perez, V Riera, D Miguel, P Campomanes, M I Menendez, T L Sordo, S Garcia-Granda

Pure And Applied Chemistry

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

34 Citations (Scopus)

Abstract

As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.

Original language	English
Pages (from-to)	3706-3707
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	13
DOIs	https://doi.org/10.1021/ja034070s
Publication status	Published - 2 Apr 2003

Keywords

imines
ketenes
beta-lactams

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10.1021/ja034070s

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title = "Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction",

abstract = "As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.",

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author = "E Hevia and J Perez and V Riera and D Miguel and P Campomanes and Menendez, {M I} and Sordo, {T L} and S Garcia-Granda",

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AU - Hevia, E

AU - Perez, J

AU - Riera, V

AU - Miguel, D

AU - Campomanes, P

AU - Menendez, M I

AU - Sordo, T L

AU - Garcia-Granda, S

PY - 2003/4/2

Y1 - 2003/4/2

N2 - As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.

AB - As depicted in the scheme, the alkylidenamido complex 1, a N-rhenaimine, reacts with ketenes to afford the β-lactams 2−4, which possess a {Re(CO)3(bpy)} fragment as substituent at nitrogen. Clean demetalations using HOTf or MeOTf yield the free β-lactams or N-methyl-β-lactams along with [Re(OTf)(CO)3(bpy)]. DFT calculations help to rationalize why the reaction is faster than those of non transition metal N-substituted imines.

KW - imines

KW - ketenes

KW - beta-lactams

U2 - 10.1021/ja034070s

DO - 10.1021/ja034070s

M3 - Article

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VL - 125

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 13

ER -

Synthesis of beta-lactams from a N-rhenaimine: effect of the transition metal on the energetic profile of the Staudinger reaction

Abstract

Keywords

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