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In this work, the stereoselective heterogeneous hydrogenation of a tetrasubstituted indolizine was studied. Partial hydrogenation products were obtained in three steps from a substituted pyridine-2-carboxaldehyde prepared from commercial pyridoxine hydrochloride. The hydrogenation of the indolizine ring was shown to be diastereoselective, forming trans-  6b and cis  -9 . Theoretical calculations ( ab initio and DFT) were used to rationalize the unusual trans stereoselectivity for 6b , and a keto-enol tautomerism under kinetic control has been proposed as the source of diastereoselectivity.

Origin of the Diastereoselectivity of the Heterogeneous Hydrogenation of a Substituted Indolizine