Catalytic enantioselective carboncarbon bond formation by addition of dialkylzinc reagents to cyclic 1,3-diene monoepoxides

Chiral copper complexes of 2,2′-binaphthyl-based phosphorus amidites are shown to be highly effective catalysts for the conjugate addition of dialkylzinc reagents to vinyloxiranes. The corresponding allylic alcohol reaction products (S N2′-pathway) were obtained with moderate to high regioselectivit...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 42; pp. 7795 - 7798
Main Authors Badalassi, Fabrizio, Crotti, Paolo, Macchia, Franco, Pineschi, Mauro, Arnold, Alexander, Feringa, Ben L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.10.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXIDES
COMPLEXES
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Summary:Chiral copper complexes of 2,2′-binaphthyl-based phosphorus amidites are shown to be highly effective catalysts for the conjugate addition of dialkylzinc reagents to vinyloxiranes. The corresponding allylic alcohol reaction products (S N2′-pathway) were obtained with moderate to high regioselectivity. Both direct- (S N2-pathway) and conjugate-opening addition (S N2′-pathway) seem to proceed with complete anti stereoselectivity. The enantioselectivity of these addition reactions according to a kinetic resolution protocol turned out to be high (>90% ee) with 1,3-cyclohexadiene and 1,3-cycloheptadiene monoepoxides. The first catalytic enantioselective ring-opening of cycloaliphatic vinyloxiranes by dialkylzinc reagents is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01704-3