Synthesize of β‑AminoEsters from Enamidesvia 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation

A 1,8-diazabicyclo[5.4.0]­undecane-7-ene (DBU)-mediated hydroalkylation of enamides with malonic acid diesters/β-carbonyl esters has been established, featuring no metal involvement, mild reaction conditions, and good functional group tolerance. The protocol enables the expedited preparation of a variety of β-amino esters. Preliminary mechanistic investigations, encompassing control experiments and capture experiments of key intermediates, have substantiated the proposed DBU-mediated hydroalkylation pathway.

Publication Details

Journal
Figshare
Published
2025-02-14
DOI
https://doi.org/10.1021/acs.joc.4c02968.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

Synthesize of β‑AminoEsters from Enamidesvia 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation

Figshare
Cyclopropane Reaction Mechanisms
article

Synthesize of β‑AminoEsters from Enamidesvia 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation

article en

Abstract

A 1,8-diazabicyclo[5.4.0]­undecane-7-ene (DBU)-mediated hydroalkylation of enamides with malonic acid diesters/β-carbonyl esters has been established, featuring no metal involvement, mild reaction conditions, and good functional group tolerance. The protocol enables the expedited preparation of a variety of β-amino esters. Preliminary mechanistic investigations, encompassing control experiments and capture experiments of key intermediates, have substantiated the proposed DBU-mediated hydroalkylation pathway.

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Clean water and sanitation
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Cyclopropane Reaction Mechanisms
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Synthesize of β‑AminoEsters from Enamidesvia 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation · Figshare (2025) | TGRS Research Map | TGRS