Facile and practical access to chiral benzofused oxa-heterocycles via asymmetric hydrogenation and intramolecular SNAr cascade

Fangyuan wang2; Ting wu1; Bin Lu1; Jianchao Yu1; Jianchao Yu1; Boxuan Yi1; Xumu Zhang1; Gen-Qiang Chen1,2

2023-12-15

10.1039/D3QO01665J

Org. Chem. Front.   影响因子和分区

2052-4129

Development of efficient protocols for the synthesis of chiral benzofused oxa-heterocycles has attracted tremendous interest due to the ubiquitous presence of these structural motifs in numerous bioactive compounds and antibiotics. Herein, we report a tandem asymmetric hydrogenation and intramolecular SNAr reaction, providing a facile and practical access to valuable six- and five-membered chiral benzofused cyclic ethers with high yields and enantioselectivities (up to 99% yield and up to 99% ee). Furthermore, the synthetic potential of the reaction was demonstrated by a gram-scale experiment.

SCI ; EI ; IC

英语

第一 ; 共同第一 ; 通讯

National Basic Research Program of China (973 Program)[2021YFF0701604] ; National Key R&D Program of China[21991113] ; National Natural Science Foundation of China[KQTD20150717103157174] ; Southern University of Science and Technology[202009251612-22002] ; Stable Support Plan Program of Shenzhen Natural Science Fund[2020B010188001] ; Key-Area Research and Development Program of Guangdong Province[2020KCXTD016] ; Innovative Team of Universities in Guangdong Province[2022B1515020055]

Chemistry

Chemistry, Organic

WOS:001135759000001

ROYAL SOC CHEMISTRY

20240215329493

Hydrogenation ; Nitrogen compounds

Chemical Reactions:802.2

人工提交

1.Medi-X Pingshan and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China
2.Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518000, People’s Republic of China

Fangyuan wang,Ting wu,Bin Lu,et al. Facile and practical access to chiral benzofused oxa-heterocycles via asymmetric hydrogenation and intramolecular SNAr cascade[J]. Org. Chem. Front.,2023,11(4).

Fangyuan wang.,Ting wu.,Bin Lu.,Jianchao Yu.,Jianchao Yu.,...&Gen-Qiang Chen.(2023).Facile and practical access to chiral benzofused oxa-heterocycles via asymmetric hydrogenation and intramolecular SNAr cascade.Org. Chem. Front.,11(4).

Fangyuan wang,et al."Facile and practical access to chiral benzofused oxa-heterocycles via asymmetric hydrogenation and intramolecular SNAr cascade".Org. Chem. Front. 11.4(2023).