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

✍ Scribed by Fabrizio Badalassi; Paolo Crotti; Franco Macchia; Mauro Pineschi; Alexander Arnold; Ben L. Feringa

Book ID: 104259990
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 228 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01704-3

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✦ Synopsis

Chiral copper complexes of 2,2'-binaphthyl-based phosphorus amidites are shown to be highly effective catalysts for the conjugate addition of dialkylzine reagents to vinyloxiranes. The corresponding allylic alcohol reaction products (SN2'-pathway) were obtained with moderate to high regioselectivity. Both direct-(SN2-pathway) and conjugate-opening addition (SN2'-pathway) seem to proceed with complete anti stereoselectivity. The enantiuseleetivity 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.

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