Enantioselective synthesis of acyclic allylic esters catalyzed by a palladium/BINAP(S) system |
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Authors: | J.W. Faller Jeremy C. Wilt |
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Affiliation: | Department of Chemistry, Yale University, New Haven, CT 06520-8107, USA |
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Abstract: | The synthesis of chiral nonracemic acyclic allylic pivalates via the Pd-catalyzed allylic substitution of racemic allylic carbonates is presented. Good to excellent enantioselectivities (up to 90%) were observed in several cases. An extraordinarily high preference for the production of the branched regioisomeric product is seen when starting from 3-buten-2-yl and crotyl substrates. A significant kinetic resolution (krel = 38) of the 1,3-dimethylallyl substrate was also observed, leading to the production of esters of both enantiomers of an allylic alcohol with a single enantiomer of catalyst. |
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Keywords: | Palladium Asymmetric allylation Catalysis |
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