Beilstein J. Org. Chem.2009,5, No. 69, doi:10.3762/bjoc.5.69
carbocation rearrangement takes place faster than any nucleophilic interception of species 21 and 22. (A hydrideshift from the bridging CH2 to carbocation 21 was also considered; however, based on the regioselective formation of compound 19b this mechanism was discounted.) The remarkable contrasting
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Graphical Abstract
Scheme 1:
The diastereoselective intramolecular Heck-hydrogenation and double reduction sequence as a means o...
Beilstein J. Org. Chem.2007,3, No. 43, doi:10.1186/1860-5397-3-43
undergoing a 1,5-(4 → 5) hydrideshift prior to cyclization to yield a 6-membered ring product 6 (Scheme 2). This is in contrast to an earlier report by Sandhu et al to obtain pyrrolo [2,3-d]pyrimidines from 6-tert-amino-substituted uracils and dimethyl acetylenedicarboxylate.[32] However, further work is in