Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones

Lu，Zhongyue; Chen，Xuling; Li，Pengfei

2023-12-01

10.1016/j.tchem.2023.100048

Tetrahedron Chem   影响因子和分区

2666-951X

A chiral sulfonamide-phosphine catalyzed regio- and enantioselective (3 + 3)-annulation of 2-(4H-benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-dihydro-3H-pyrazol-3-ones has been established, affording a wide range of such 1,4,5,6-tetrahydropyrano [2,3-c]pyrazole-containing carboxylates in generally high yields (61–96%) with high diastereo- and enantioselectivities (8:1->20:1 dr, 85–95% ee). Based on several control experiments, a reaction mechanism was proposed. Importantly, the work represents the first example of using benzoxazinyl acrylates as three-atom synthons, which enriches the chemistry of benzoxazinyl acrylates.

Annulation Asymmetric organocatalysis Benzooxazine Carboxylates Pyrazolones

英语

第一 ; 通讯

2-s2.0-85174946779

Scopus

Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,College of Science,Southern University of Science and Technology Guangming Advanced Research Institute,Southern University of Science and Technology (SUSTech),518055,China

Lu，Zhongyue,Chen，Xuling,Li，Pengfei. Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones[J]. Tetrahedron Chem,2023,8.

Lu，Zhongyue,Chen，Xuling,&Li，Pengfei.(2023).Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones.Tetrahedron Chem,8.

Lu，Zhongyue,et al."Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones".Tetrahedron Chem 8(2023).