Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates

[Image: see text] A highly efficient N,P-ligated iridium complex is presented for the simple preparation of chiral tetrahydro-3-benzazepine motifs by catalytic asymmetric hydrogenation. Substrates bearing both 1-aryl and 1-alkyl substituents were smoothly converted to the corresponding hydrogenated...

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Autores principales: Peters, Bram B. C., Andersson, Pher G., Ruchirawat, Somsak, Ieawsuwan, Winai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8938950/
https://www.ncbi.nlm.nih.gov/pubmed/35238569
http://dx.doi.org/10.1021/acs.orglett.2c00362
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author Peters, Bram B. C.
Andersson, Pher G.
Ruchirawat, Somsak
Ieawsuwan, Winai
author_facet Peters, Bram B. C.
Andersson, Pher G.
Ruchirawat, Somsak
Ieawsuwan, Winai
author_sort Peters, Bram B. C.
collection PubMed
description [Image: see text] A highly efficient N,P-ligated iridium complex is presented for the simple preparation of chiral tetrahydro-3-benzazepine motifs by catalytic asymmetric hydrogenation. Substrates bearing both 1-aryl and 1-alkyl substituents were smoothly converted to the corresponding hydrogenated product with excellent enantioselectivity (91–99% ee) and in isolated yield (92–99%). The synthetic value of this transformation was demonstrated by a gram-scale hydrogenation and application in the syntheses of trepipam and fenoldopam.
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spelling pubmed-89389502022-03-28 Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates Peters, Bram B. C. Andersson, Pher G. Ruchirawat, Somsak Ieawsuwan, Winai Org Lett [Image: see text] A highly efficient N,P-ligated iridium complex is presented for the simple preparation of chiral tetrahydro-3-benzazepine motifs by catalytic asymmetric hydrogenation. Substrates bearing both 1-aryl and 1-alkyl substituents were smoothly converted to the corresponding hydrogenated product with excellent enantioselectivity (91–99% ee) and in isolated yield (92–99%). The synthetic value of this transformation was demonstrated by a gram-scale hydrogenation and application in the syntheses of trepipam and fenoldopam. American Chemical Society 2022-03-03 2022-03-18 /pmc/articles/PMC8938950/ /pubmed/35238569 http://dx.doi.org/10.1021/acs.orglett.2c00362 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Peters, Bram B. C.
Andersson, Pher G.
Ruchirawat, Somsak
Ieawsuwan, Winai
Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title_full Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title_fullStr Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title_full_unstemmed Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title_short Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
title_sort synthesis of chiral tetrahydro-3-benzazepine motifs by iridium-catalyzed asymmetric hydrogenation of cyclic ene-carbamates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8938950/
https://www.ncbi.nlm.nih.gov/pubmed/35238569
http://dx.doi.org/10.1021/acs.orglett.2c00362
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