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Some Observations Regarding the Stereochemical Course of Iminium Ion Reductions: An Example of the Size Difference Between Sodium Cyanoborohydride and Sodium Triacetoxyborohydride
The stereochemical course of reductions of iminium ions with sodium cyanoborohydride and sodium triacetoxyborohydride was examined within the context of model studies directed toward the synthesis of the quinolizidine alkaloid clavepictine A. Conformational preferences of the iminium ion and and effective size of the reducing agent were shown play a role in determining reduction stereochemistry.