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

ABSTRACT: 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.

SUBMITTER: Lou Y

PROVIDER: S-EPMC8146211 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Catalytic asymmetric hydrogenation of (<i>Z</i>)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Lou Yazhou Y Wang Jun J Gong Gelin G Guan Fanfu F Lu Jiaxiang J Wen Jialin J Zhang Xumu X

Chemical science 20191125 3

The direct catalytic asymmetric hydrogenation of (<i>Z</i>)-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 ...[more]

PMID: 34123062

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