Selectivity and reactivity in asymmetric allylic alkylation
1999 (English)In: Pure and Applied Chemistry, ISSN 0033-4545, E-ISSN 1365-3075, Vol. 71, no 8, 1477-1483 p.Article in journal (Refereed) PublishedText
2-(1-Hydroxyalkyl)-6-oxazolyl-and 2-(1-alkoxyalkyl)-6-oxazolylpyridines serve as versatile ligands in the palladium-catalyzed allylic substitution of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate as nucleophile. The enantioselectivity of the reaction is dependent on the conformation of the ligands, as deduced by NMR, X-ray crystallography and DFT calculations of palladium(II) complexes of the ligands. The reactions are slow, requiring up to four days reaction time. However, with the use of microwave flash heating, reaction times are reduced to 2 min, with only minor loss in stereoselectivity.
Place, publisher, year, edition, pages
Royal Inst Technol, Dept Chem, SE-10044 Stockholm, Sweden. Royal Danish Sch Pharm, DK-2100 Copenhagen, Denmark. Uppsala Univ, Ctr Biomed, Dept Organ Pharmaceut Chem, SE-75123 Uppsala, Sweden. Stockholm Univ, Arrhenius Lab, Dept Struct Chem, SE-10691 Stockholm, Sweden., 1999. Vol. 71, no 8, 1477-1483 p.
IdentifiersURN: urn:nbn:se:uu:diva-275389DOI: 10.1351/pac199971081477ISI: 000086016000013OAI: oai:DiVA.org:uu-275389DiVA: diva2:900245
10th IUPAC Symposium on Organo-Metallic Chemistry Directed Toward Organic Synthesis (OMCOS 10), JUL 18-22, 1999, VERSAILLES, FRANCE