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Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2017 Feb 01; Vol. 56 (6), pp. 1520-1524. Date of Electronic Publication: 2017 Jan 12. - Publication Year :
- 2017
-
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.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Alkadienes chemical synthesis
Alkadienes chemistry
Allyl Compounds chemistry
Anti-Retroviral Agents chemistry
Catalysis
Dideoxynucleosides chemistry
Models, Molecular
Purines chemistry
Rhodium chemistry
Stereoisomerism
Allyl Compounds chemical synthesis
Anti-Retroviral Agents chemical synthesis
Dideoxynucleosides chemical synthesis
Purines chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 56
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 28079946
- Full Text :
- https://doi.org/10.1002/anie.201610876