Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine
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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.
Cormanich , R A , Zeoly , L A , Santos , H , Camilo , N S , Bühl , M & Coelho , F 2020 , ' Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine ' , Journal of Organic Chemistry , vol. 85 , no. 17 , pp. 11541-11548 . https://doi.org/10.1021/acs.joc.0c01338
Journal of Organic Chemistry
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DescriptionThe authors are grateful to FAPESP for the financial support of this research. The authors also thank FAPESP for the fellowships to R.A.C. (#2018/03910-1) and F.C. (#2013/07600-3 and #2018/02611-3) and for a scholarship to H.S. (#2015/09205-0) and CNPq for a scholarship to L.A.Z. and a research fellowship for F.C, (307840/2014-0, 422890/2016-2 and 301330/2016-2). L.A.Z. also thanks Capes for a scholarship.
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