Formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles. Issue 1 (27th October 2016)

• Record Type: Journal Article
• Authors: Peng, Xiao-Jiao; Ho, Yee Ann; Wang, Zhi-Peng; Shao, Pan-Lin; Zhao, Yu; He, Yun
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 1(2017)
• Page Start: 81
• Page End: 85
• Publication Date: 2016-10-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00555a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The first formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates with methyleneindolinones was developed. A variety of optically enriched 3, 3′-pyrrolidinyl spirooxindoles were obtained. Abstract : The first enantioselective formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates with protecting-group-free methyleneindolinones was developed. A variety of optically enriched 3, 3′-pyrrolidinyl spirooxindoles were obtained in excellent yields, and diastereo- and enantioselectivities (up to 99% yield, >20 : 1 dr, 99% ee) with low catalyst loading under mild reaction conditions.