Journal
TETRAHEDRON-ASYMMETRY
Volume 18, Issue 3, Pages 406-413Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2007.01.014
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Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enantiomeric excesses of the isolated alkaloids were determined from their H-1 NMR spectra measured in the presence of (+)-(R)-tert-butylphenylphosphinothio(seleno)ic acids as chiral solvating agents. The absolute configurations at the newly created stereogenic carbon atoms were confirmed, in all cases, by X-ray crystallography. (c) 2007 Elsevier Ltd. All rights reserved.
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