Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine

Rodrigo A. Cormanich, Lucas A. Zeoly, Hugo Santos, Nilton S. Camilo, Michael Bühl, Fernando Coelho

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Abstract

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.
Original languageEnglish
Pages (from-to)11541-11548
Number of pages8
JournalThe Journal of Organic Chemistry
Volume85
Issue number17
Early online date11 Aug 2020
DOIs
Publication statusPublished - 4 Sept 2020

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