Palladium-Catalyzed Diastereoselective Formal [5+3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring

Niu, Ben1,2; Wu, Xiao-Yun1,2; Wei, Yin4; Shi, Min1,2,3,4

2019-06-21

10.1021/acs.orglett.9b01748

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

A Pd-catalyzed formal [5 + 3] intermolecular cycloaddition reaction of isatin-derived alpha-(trifluoromethyl)-imines with aryl substituted vinylethylene carbonates (VECs) has been reported, affording trifluoromethyl-group-containing spirooxindoles fused with an eight-membered ring as a single diastereoisomer in good yields in the presence of a Bronsted acid in a one-pot manner under mild conditions. The asymmetric version of this reaction has been also realized using a chiral phosphine ligand along with the further transformation of the obtained product to give a spirooxindolo pyrrolidine derivative upon oxidation.

SCI ; IC ; CCR

英语

NI期刊

通讯

[sioczz201808]

Chemistry

Chemistry, Organic

WOS:000473116000097

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
2.East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China
4.Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China

Niu, Ben,Wu, Xiao-Yun,Wei, Yin,et al. Palladium-Catalyzed Diastereoselective Formal [5+3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring[J]. ORGANIC LETTERS,2019,21(12):4859-4863.

Niu, Ben,Wu, Xiao-Yun,Wei, Yin,&Shi, Min.(2019).Palladium-Catalyzed Diastereoselective Formal [5+3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring.ORGANIC LETTERS,21(12),4859-4863.

Niu, Ben,et al."Palladium-Catalyzed Diastereoselective Formal [5+3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring".ORGANIC LETTERS 21.12(2019):4859-4863.