Microwave-assisted organocatalysis: phosphine-mediated Tomita Zipper cyclization affording functionalized spirooxindole. Issue 33 (17th August 2016)

• Record Type: Journal Article
• Authors: Zhang, Xiao-Yan; Shen, Ze; Hu, Li-Li; Wang, Liang-Jun; Lin, You-Shuai; Xie, Jian-Wu; Cui, Hai-Lei
• Is Part Of: Tetrahedron letters. Volume 57:Issue 33(2016)
• Page Start: 3790
• Page End: 3794
• Publication Date: 2016-08-17
• Subjects: Tomita Zipper cyclization -- Microwave -- Phosphine -- Spirooxindole -- Dicyanomethylideneoxindole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.07.035
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A phosphine-mediated Tomita Zipper cyclization has been developed. The in situ generated α-nucleophile as key intermediate is proposed. Moderate to good yields and diastereoselectivities can be achieved. Abstract: A microwave-assisted and phosphine-mediated Tomita Zipper cyclization of dicyanomethylideneoxindoles and ynones has been developed. Various functionalized spirooxindoles with five-membered carbocyclic ring can be obtained in moderate to good yields with moderate to excellent diastereoselectivities through in situ generation of α-nucleophile (up to 87% yield, >20:1 dr).