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Beilstein J. Org. Chem. 2015, 11, 1060–1067, doi:10.3762/bjoc.11.119
Graphical Abstract
Scheme 1: The Aubé reaction and its selected applications.
Figure 1: Selective carbocyclic nucleoside analogues from the literature and our initial designs.
Scheme 2: Top: synthesis of azido alcohol derivative 3 and bottom: structural elucidation of the minor diaste...
Scheme 3: Aubé reaction of cylopentenyl azido alcohol 3 with cyclohexanone.
Scheme 4: Substrate scope of the reaction: preparation of cyclopentene-substituted lactams and key NMR correl...
Scheme 5: Proposed mechanism for the Aubé reaction for azido alcohols embedded in a cyclopentene system.
Scheme 6: Hydroxylated cyclopentyl-substituted lactams.
Figure 2: ORTEP plot of triol (±)-12.