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Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters

The direct catalytic asymmetric hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and...

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Autores principales: Lou, Yazhou, Wang, Jun, Gong, Gelin, Guan, Fanfu, Lu, Jiaxiang, Wen, Jialin, Zhang, Xumu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8146211/
https://www.ncbi.nlm.nih.gov/pubmed/34123062
http://dx.doi.org/10.1039/c9sc04534a
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author Lou, Yazhou
Wang, Jun
Gong, Gelin
Guan, Fanfu
Lu, Jiaxiang
Wen, Jialin
Zhang, Xumu
author_facet Lou, Yazhou
Wang, Jun
Gong, Gelin
Guan, Fanfu
Lu, Jiaxiang
Wen, Jialin
Zhang, Xumu
author_sort Lou, Yazhou
collection PubMed
description The direct catalytic asymmetric hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and 99% ee). The utility of the products has been demonstrated by transformation to their corresponding boronic acid derivatives by a Pd-catalyzed borylation reaction and an efficient synthesis of a potential intermediate of bortezomib. The clean, atom-economic and environment friendly nature of this catalytic asymmetric hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic esters of great potential in the area of organic synthesis and medicinal chemistry.
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spelling pubmed-81462112021-06-11 Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters Lou, Yazhou Wang, Jun Gong, Gelin Guan, Fanfu Lu, Jiaxiang Wen, Jialin Zhang, Xumu Chem Sci Chemistry The direct catalytic asymmetric hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and 99% ee). The utility of the products has been demonstrated by transformation to their corresponding boronic acid derivatives by a Pd-catalyzed borylation reaction and an efficient synthesis of a potential intermediate of bortezomib. The clean, atom-economic and environment friendly nature of this catalytic asymmetric hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic esters of great potential in the area of organic synthesis and medicinal chemistry. The Royal Society of Chemistry 2019-11-25 /pmc/articles/PMC8146211/ /pubmed/34123062 http://dx.doi.org/10.1039/c9sc04534a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Lou, Yazhou
Wang, Jun
Gong, Gelin
Guan, Fanfu
Lu, Jiaxiang
Wen, Jialin
Zhang, Xumu
Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title_full Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title_fullStr Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title_full_unstemmed Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title_short Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
title_sort catalytic asymmetric hydrogenation of (z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8146211/
https://www.ncbi.nlm.nih.gov/pubmed/34123062
http://dx.doi.org/10.1039/c9sc04534a
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