Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

Gong, Quan1; Wen, Jialin1,2; Zhang, Xumu1,3

2019-07-07

10.1039/c9sc01769k

Chemical Science   影响因子和分区

2041-6520

2041-6539

We herein report an efficient method to synthesize cyclic hydroxy ketones with a chiral quaternary center. Catalyzed by an Ir/f-ampha complex, cyclic alpha,alpha-disubstituted 1,3-diketones were hydrogenated, giving mono-reduced products with both high enantioselectivities and diastereoselectivities. In addition, C = C and C = C bonds could survive in this catalytic system. This method was applied in the preparation of (+)-estrone. No diols were observed in this chemical transformation. The enantiomeric and diastereomeric induction were achieved as a result of steric hindrance.

SCI ; EI ; IC ; CCR

英语

NI期刊 ; NI论文

第一 ; 通讯

Shenzhen Commission of Science, Technology and Innovation[JCYJ20170817104853520] ; Shenzhen Commission of Science, Technology and Innovation[JSGG20160608140847864]

Chemistry

Chemistry, Multidisciplinary

WOS:000473055300012

ROYAL SOC CHEMISTRY

20192707134495

Carbon ; Catalysis ; Iridium compounds ; Ketones ; Stereochemistry

Chemistry:801 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

Gong, Quan,Wen, Jialin,Zhang, Xumu. Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon[J]. Chemical Science,2019,10(25):6350-6353.

Gong, Quan,Wen, Jialin,&Zhang, Xumu.(2019).Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon.Chemical Science,10(25),6350-6353.

Gong, Quan,et al."Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon".Chemical Science 10.25(2019):6350-6353.