Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 6, Pages 1520-1524Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610876
Keywords
abacavir; allenes; asymmetric catalysis; carbanucleoside; rhodium
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Funding
- DFG
- Fonds der Chemischen Industrie
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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.
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