Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents of α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes

The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) were obtained with structurally rigi...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 31; pp. 5803 - 5806
Main Authors Versleijen, Jos P.G., van Leusen, Albert M., Feringa, Ben L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.07.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOZINC REAGENTS
ENONES
PHOSPHORUS LIGANDS
ORGANIC-SYNTHESIS
ALPHA-AMINO-ACIDS
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Summary:The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) were obtained with structurally rigid 3-nitrocoumarins, leading to a new route to optically active β-aryl-nitroalkanes. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01118-1