title: Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir.
abstract: The rhodium-catalyzed atom-economic asymmetric N-selective intermolecular addition of purine derivatives to terminal allenes is reported. Branched allylic purines were obtained in high yields, regioselectivity and outstanding enantioselectivity utilizing a Rh/Josiphos catalyst. Conversely, linear selective allylation of purines could be realized in good to excellent regio- and E/Z-selectivity with a Pd/dppf catalyst system. Furthermore, the new methodology was applied to a straightforward asymmetric synthesis of carbocyclic nucleoside abacavir.
authors.affiliation: Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Alberstr. 21, 79104, Freiburg, Germany.
authors.forename: Niels
authors.initials: N
authors.lastname: Thieme
authors.affiliation: Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Alberstr. 21, 79104, Freiburg, Germany.
authors.forename: Bernhard
authors.identifier: 0000-0002-2514-3898
authors.initials: B
authors.lastname: Breit
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D044966:Anti-Retroviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D000099227:Abacavir
chemical_list: D000466:Alkadienes; D000498:Allyl Compounds; D044966:Anti-Retroviral Agents; D015224:Dideoxynucleosides; D011687:Purines; D012238:Rhodium; D000099227:Abacavir
keywords: abacavir; allenes; asymmetric catalysis; carbanucleoside; rhodium