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

doi:10.1021/acs.joc.0c01338

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	11541-11548
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	85
Issue number	17
Early online date	11 Aug 2020
DOIs	https://doi.org/10.1021/acs.joc.0c01338
Publication status	Published - 4 Sept 2020

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Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine (dataset)
Buehl, M. (Creator), PANGEA, 2020
DOI: 10.1594/PANGAEA.881019
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@article{f2bbb589c140473bad133f1b3cf60bc0,

title = "Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine",

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.",

author = "Cormanich, \{Rodrigo A.\} and Zeoly, \{Lucas A.\} and Hugo Santos and Camilo, \{Nilton S.\} and Michael B{\"u}hl and Fernando Coelho",

note = "The 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. ",

year = "2020",

month = sep,

day = "4",

doi = "10.1021/acs.joc.0c01338",

language = "English",

volume = "85",

pages = "11541--11548",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "17",

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TY - JOUR

T1 - Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine

AU - Cormanich, Rodrigo A.

AU - Zeoly, Lucas A.

AU - Santos, Hugo

AU - Camilo, Nilton S.

AU - Bühl, Michael

AU - Coelho, Fernando

N1 - The 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.

PY - 2020/9/4

Y1 - 2020/9/4

N2 - 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.

AB - 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.

U2 - 10.1021/acs.joc.0c01338

DO - 10.1021/acs.joc.0c01338

M3 - Article

SN - 0022-3263

VL - 85

SP - 11541

EP - 11548

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 17

ER -

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

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Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine (dataset)

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