Journal of Organic Chemistry p. 11541 - 11548 (2020)
Update date:2022-09-26
Topics:
Cormanich, Rodrigo A.
Zeoly, Lucas A.
Santos, Hugo
Camilo, Nilton S.
Bühl, Michael
Coelho, Fernando
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.
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