Synthesis of chiral binaphthalenes using the asymmetric Suzuki reaction

Andrew N. Cammidge, Karen V. L. Crépy

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The synthesis of atropisomeric 1,1'-binaphthalenes can be achieved using an asymmetric Suzuki cross-coupling reaction. The Suzuki reaction leading to such hindered compounds is challenging and competing hydrolytic deboronation frequently dominates unless carefully chosen conditions are employed. The simple, standard mechanism is inadequate when describing the Suzuki coupling of hindered partners. Evidence suggests that the key step leading to asymmetry is transmetallation (delivery of the organometallic by the asymmetric ligand) and the reactions operate under kinetic control. Reductive elimination (itself likely to be triggered by oxidative addition of another molecule of halide) is fast compared with equilibration (epimerisation and/or cis–trans isomerisation).
Original languageEnglish
Pages (from-to)4377-4386
Number of pages10
Issue number20
Publication statusPublished - 2004

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