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Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir
Author(s) -
Thieme Niels,
Breit Bernhard
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610876
Subject(s) - enantioselective synthesis , chemistry , regioselectivity , abacavir , allylic rearrangement , catalysis , stereochemistry , selectivity , purine metabolism , rhodium , combinatorial chemistry , organic chemistry , lamivudine , enzyme , hepatitis b virus , virus , virology , biology
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.