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Asymmetric Nickel-catalyzed Cross-coupling Reaction of Allylic Substrates with Grignard Reagents by Giambattista Consiglio; Oreste Piccolo; Lucia Roncetti; Franco Morandini is a Chemistry article available to read on EtoBox.

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Two possible routes for the synthesis of optically active olefinit compounds through cross-coupling reaction between allylic electrophiles and Grignard reagents catalyzed by nickel complexes containing chiral diphosphine ligands were investigated: i) the reaction of chiral racemic (or prochiral) allylic compounds with achiral Grignard reagents and ii) the reaction of chiral Grignard reagents with ally1 electrophiles. Optical yields higher than 90% were obtained for the first reaction route (compound 11) and up to 58% (compound 24) were obtained for the second route, using a C2 chiral ligand. namely (S,S)-l,2-dimethyl-l,2-ethanediylbis(diphenylphosphine). It has long been known that olefinic compounds oxidized at the allylic position such as alcohols, ethers or esters are activated toward nucleophilic substitution by palladium or nickel compounds mostly containing phosphine ligands. 112 Stereochemical investigations have found either retention or inversion of configuration for these reactions depending on the incoming nucleophile. 3 Indeed, the stereochemistry of the reaction products is a consequence of an "anti" attack of the metal catalyst on the allylic substrate followed by an

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Author

Giambattista Consiglio; Oreste Piccolo; Lucia Roncetti; Franco Morandini

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1986

Language

EN

Field

Chemistry (Physical Sciences)