Nickel(II)-catalyzed Michael additions. Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4- benzyloxazolidin-2-one

Jaume Clariana; Nicanor Gálvez; Caroline Marchi; Marcial Moreno-Mañas; Adelina Vallribera; Elies Molins

doi:10.1016/S0040-4020(99)00358-0

Nickel(II)-catalyzed Michael additions. Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4- benzyloxazolidin-2-one

Jaume Clariana, Nicanor Gálvez, Caroline Marchi, Marcial Moreno-Mañas, Adelina Vallribera, Elies Molins

Department of Chemistry

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

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Abstract

Ni(acac)2 and Ni(salicylaldehydate)2 are effective catalysts for conjugate additions of 2-methyl-1,3-dicarbonyl compounds to Michael acceptors. Significant diastereomeric excesses are obtained in the Michael additions of enantiopure N-acetoacetyl-4-benzyloxazolidinones. Reaction of the latter compound with aryl isocyanates affords unsymmetrical diamides of malonic acid.

Original language	English
Pages (from-to)	7331-7344
Journal	Tetrahedron
Volume	55
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4020(99)00358-0
Publication status	Published - 4 Jun 1999

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title = "Nickel(II)-catalyzed Michael additions. Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4- benzyloxazolidin-2-one",

abstract = "Ni(acac)2 and Ni(salicylaldehydate)2 are effective catalysts for conjugate additions of 2-methyl-1,3-dicarbonyl compounds to Michael acceptors. Significant diastereomeric excesses are obtained in the Michael additions of enantiopure N-acetoacetyl-4-benzyloxazolidinones. Reaction of the latter compound with aryl isocyanates affords unsymmetrical diamides of malonic acid.",

author = "Jaume Clariana and Nicanor G{\'a}lvez and Caroline Marchi and Marcial Moreno-Ma{\~n}as and Adelina Vallribera and Elies Molins",

year = "1999",

month = jun,

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doi = "10.1016/S0040-4020(99)00358-0",

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T1 - Nickel(II)-catalyzed Michael additions. Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4- benzyloxazolidin-2-one

AU - Clariana, Jaume

AU - Gálvez, Nicanor

AU - Marchi, Caroline

AU - Moreno-Mañas, Marcial

AU - Vallribera, Adelina

AU - Molins, Elies

PY - 1999/6/4

Y1 - 1999/6/4

N2 - Ni(acac)2 and Ni(salicylaldehydate)2 are effective catalysts for conjugate additions of 2-methyl-1,3-dicarbonyl compounds to Michael acceptors. Significant diastereomeric excesses are obtained in the Michael additions of enantiopure N-acetoacetyl-4-benzyloxazolidinones. Reaction of the latter compound with aryl isocyanates affords unsymmetrical diamides of malonic acid.

AB - Ni(acac)2 and Ni(salicylaldehydate)2 are effective catalysts for conjugate additions of 2-methyl-1,3-dicarbonyl compounds to Michael acceptors. Significant diastereomeric excesses are obtained in the Michael additions of enantiopure N-acetoacetyl-4-benzyloxazolidinones. Reaction of the latter compound with aryl isocyanates affords unsymmetrical diamides of malonic acid.

U2 - 10.1016/S0040-4020(99)00358-0

DO - 10.1016/S0040-4020(99)00358-0

M3 - Article

SN - 0040-4020

VL - 55

SP - 7331

EP - 7344

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Nickel(II)-catalyzed Michael additions. Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4- benzyloxazolidin-2-one

Abstract

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