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

Lou，Yazhou1; Wang，Jun1; Gong，Gelin1; Guan，Fanfu1; Lu，Jiaxiang1; Wen，Jialin1,2; Zhang，Xumu1

2020

10.1039/c9sc04534a

Chemical Science   影响因子和分区

2041-6520

2041-6539

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.

SCI ; IC ; CCR ; EI

英语

NI论文

第一 ; 通讯

Science, Technology and Innovation Commission of Shenzhen Municipality[]

Chemistry

Chemistry, Multidisciplinary

WOS:000508917000026

Royal Society of Chemistry

20200508105671

Esters ; Reaction intermediates

Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Organic Compounds:804.1

2-s2.0-85078534936

Scopus

1.Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen, Guangdong,518055,China
2.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,518000,China

Lou，Yazhou,Wang，Jun,Gong，Gelin,et al. Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: Direct route to alkyl-substituted α-amidoboronic esters[J]. Chemical Science,2020,11(3):851-855.

Lou，Yazhou.,Wang，Jun.,Gong，Gelin.,Guan，Fanfu.,Lu，Jiaxiang.,...&Zhang，Xumu.(2020).Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: Direct route to alkyl-substituted α-amidoboronic esters.Chemical Science,11(3),851-855.

Lou，Yazhou,et al."Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: Direct route to alkyl-substituted α-amidoboronic esters".Chemical Science 11.3(2020):851-855.