Organocatalytic [3+2] Cycloadditions of Barbiturate‐Based Olefins with 3‐Isothiocyanato Oxindoles: Highly Diastereoselective and Enantioselective Synthesis of Dispirobarbiturates. Issue 16 (13th July 2016)

• Record Type: Journal Article
• Authors: Zhao, Hong‐Wu; Tian, Ting; Pang, Hai‐Liang; Li, Bo; Chen, Xiao‐Qin; Yang, Zhao; Meng, Wei; Song, Xiu‐Qing; Zhao, Yu‐Di; Liu, Yue‐Yang
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 16(2016)
• Page Start: 2619
• Page End: 2630
• Publication Date: 2016-07-13
• Subjects: asymmetric catalysis -- cyclization -- diastereoselectivity -- domino reactions -- enantioselectivity -- organic catalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600270
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Catalyzed by a Cinchona ‐based thiourea, the [3+2] cycloadditions of barbiturate‐based olefins with 3‐isothiocyanatooxindoles proceeded readily, and furnished dispirobarbiturates in excellent chemical yields with excellent diastereo‐ and enantioselectivities. The absolute configuration of dispirobarbiturates was firmly confirmed by an X‐ray single crystal structure analysis. A reaction mechanism was proposed to account for the enantioselective formation of dispirobarbiturates. Abstract :