Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: Scope and applications

Vijaykumar More; Antonia Di Mola; Gianluca Croce; Consiglia Tedesco; Carmen Petronzi; Antonella Peduto; Paolo De Caprariis; Rosanna Filosa; Antonio Massa

doi:10.1039/c1ob06229h

Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: Scope and applications

Vijaykumar More, Antonia Di Mola, Gianluca Croce, Consiglia Tedesco, Carmen Petronzi, Antonella Peduto, Paolo De Caprariis, Rosanna Filosa, Antonio Massa

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Simple and effective multi-component one-pot aldol addition/protection reactions of β-ketoesters to a series of aldehydes in the presence Me ₃SiCl and i-Pr ₂EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.

Lingua originale	Inglese
pagine (da-a)	8483-8488
Numero di pagine	6
Rivista	Organic and Biomolecular Chemistry
Volume	9
Numero di pubblicazione	24
DOI	https://doi.org/10.1039/c1ob06229h
Stato di pubblicazione	Pubblicato - 21 dic 2011
Pubblicato esternamente	Sì

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title = "Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: Scope and applications",

abstract = "Simple and effective multi-component one-pot aldol addition/protection reactions of β-ketoesters to a series of aldehydes in the presence Me 3SiCl and i-Pr 2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.",

author = "Vijaykumar More and {Di Mola}, Antonia and Gianluca Croce and Consiglia Tedesco and Carmen Petronzi and Antonella Peduto and {De Caprariis}, Paolo and Rosanna Filosa and Antonio Massa",

year = "2011",

month = dec,

day = "21",

doi = "10.1039/c1ob06229h",

language = "English",

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T1 - Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes

T2 - Scope and applications

AU - More, Vijaykumar

AU - Di Mola, Antonia

AU - Croce, Gianluca

AU - Tedesco, Consiglia

AU - Petronzi, Carmen

AU - Peduto, Antonella

AU - De Caprariis, Paolo

AU - Filosa, Rosanna

AU - Massa, Antonio

PY - 2011/12/21

Y1 - 2011/12/21

N2 - Simple and effective multi-component one-pot aldol addition/protection reactions of β-ketoesters to a series of aldehydes in the presence Me 3SiCl and i-Pr 2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.

AB - Simple and effective multi-component one-pot aldol addition/protection reactions of β-ketoesters to a series of aldehydes in the presence Me 3SiCl and i-Pr 2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.

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U2 - 10.1039/c1ob06229h

DO - 10.1039/c1ob06229h

M3 - Article

SN - 1477-0520

VL - 9

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EP - 8488

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: Scope and applications

Abstract

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