A P,N ligand with central and axial chiral elements: synthesis and application in allylic alkylation |
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| Institution: | 1. Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678, Clausthal-Zellerfeld, Germany;2. University of Helsinki, Department of Chemistry, P.O. Box 55, FIN-00014, Helsinki, Finland;3. Clausthal University of Technology, Institute of Technical Chemistry, Arnold-Sommerfeld-Str. 4, D-38678, Clausthal-Zellerfeld, Germany |
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| Abstract: | Two epimers of 4-({5-(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl)-4,5-dihydro-3H-dinaphtho1,2-e:2′,1′-c]azepine were prepared starting from (2S,3S)-4-amino-2,3-O-isopropylidenebutane-1,2,3-triol and (R)- and (S)-binaphthol. These ligands, in association with Pd(0) gave enantioselectivities up to 89% (S) and 36% (R) ee for the (SA,4S,5R) and the (RA,4S,5R) ligands in the alkylation of racemic 1,3-diphenylprop-2-enyl acetate with dimethyl malonate, showing that the binaphthyl moiety is the most important structure in the enantioselective creation of the new stereogenic center. |
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