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(+)-Camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc

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TLDR
In this paper, the amino alcohols were employed as chiral ligands in the nickel catalyzed conjugate additions of diethylzinc to chalcone and cyclohexenone as model substrates.
Abstract
Several novel tri- and tetradentate amino alcohol ligands, all derived from (+)-camphor, have been synthesized by using specific N -alkylation procedures. The amino alcohols were employed as chiral ligands in the nickel catalyzed conjugate additions of diethylzinc to chalcone and cyclohexenone as model substrates. For the acyclic enone enantioselectivities up to 83% were achieved.

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University of Groningen
(+)-camphor-derived tri- and tetradentate amino alcohols; synthesis and application as
ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc
Vries, André H.M. de; Imbos, Rosalinde; Feringa, Bernard
Published in:
Tetrahedron-Asymmetry
DOI:
10.1016/S0957-4166(97)00145-6
IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from
it. Please check the document version below.
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Publication date:
1997
Link to publication in University of Groningen/UMCG research database
Citation for published version (APA):
Vries, A. H. M. D., Imbos, R., & Feringa, B. (1997). (+)-camphor-derived tri- and tetradentate amino
alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of
diethylzinc.
Tetrahedron-Asymmetry
,
8
(9), 1467-1473. https://doi.org/10.1016/S0957-4166(97)00145-6
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Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis.

TL;DR: It is shown here how the structure of the C−O Bond Formation following C−H Bond Oxidation following Baeyer−Villiger-type Reaction and Wacker-type Cyclization influenced the formation of the S−N Bond Formation.
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Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

TL;DR: The breakthrough is presented using chiral phosphoramidite ligands for copper-catalyzed dialkylzinc additions for enantioselective carbon-carbon bond formation by 1,4-addition of organometallic reagents to enones.
Journal ArticleDOI

Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents using Copper-Phosphoramidite Complexes; Ligand Variation and Non-linear Effects

TL;DR: In this paper, a variety of chiral phosphoramidites were synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol.
Journal ArticleDOI

Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

TL;DR: The copper-II catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α-α-β-β, β-tetraphenyl-2,2′-dimethyl-1,3-dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.g. up to 71% for cyclohexenone and up to 62% for
References
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Book

Asymmetric synthesis

Garry Procter
Book

Conjugate Addition Reactions in Organic Synthesis

P. Perlmutter
TL;DR: In this article, the authors present a survey of conjugate receptors and their interaction with the nucleophiles, as well as a classification of reaction types and their relations with each other.
Journal ArticleDOI

Asymmetric conjugate addition

Journal ArticleDOI

Asymmetric michael addition of malonate anions to prochiral acceptors catalyzed by l-proline rubidium salt

TL;DR: In this paper, Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals, which can be applied to a wide range of substrates to give adducts with a p...
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