Efficient preparation of ( Z)-alkenyl derivatives from ( Z)-vinyl ( N, N-diisopropyl)carbamate via Ni-catalysed coupling reactions

A ( Z)-vinyl ( N, N-diisopropyl)carbamate treated with Grignard reagents, under Wenkert Nickel-catalysed conditions, gave access to several substituted ( Z)-alkenyl derivatives. These Nickel-catalysed reactions, carried out with vinyl-, phenyl-, p-methoxyphenyl-, trimethylsilylmethylmagnesium bromid...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 40; pp. 7553 - 7556
Main Authors Porée, François-Hugues, Clavel, Alexandre, Betzer, Jean-François, Pancrazi, Ange, Ardisson, Janick
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.09.2003
Elsevier
Subjects
( Z)-vinyl ( N, N-diisopropyl)carbamate
Chemical Sciences
Chemistry
Chemistry, Organic
Grignard reagent
Hoppe allylation
Nickel-catalysis
Organic chemistry
Physical Sciences
Science & Technology
Wenkert cross-coupling reaction
( Z)-vinyl ( N, N-diisopropyl)carbamate
Wenkert cross-coupling reaction
Grignard reagent
Nickel-catalysis
Hoppe allylation
ORGANIC-SYNTHESIS
ENOL ETHERS
NITROGEN DERIVATIVES
HOMOALLYLIC ALCOHOLS
CARBON-CARBON BONDS
(Z)-vinyl (N,N-diisopropyl)carbamate
OXYGEN
HOMOALDOL REACTION
OLEFINS
LITHIATION
GRIGNARD-REAGENTS
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Summary:A ( Z)-vinyl ( N, N-diisopropyl)carbamate treated with Grignard reagents, under Wenkert Nickel-catalysed conditions, gave access to several substituted ( Z)-alkenyl derivatives. These Nickel-catalysed reactions, carried out with vinyl-, phenyl-, p-methoxyphenyl-, trimethylsilylmethylmagnesium bromide and benzylmagnesium chloride, led to the corresponding ( Z)-alkenyl derivatives in good yields and high stereoselectivities. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01804-5