Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles via novel [3 + 2] annulation of isoindigos and MBH carbonates. Issue 8 (1st February 2018)

• Record Type: Journal Article
• Authors: Ren, Hong-Xia; Peng, Lin; Song, Xiang-Jia; Liao, Li-Guo; Zou, Ying; Tian, Fang; Wang, Li-Xin
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 8(2018)
• Page Start: 1297
• Page End: 1304
• Publication Date: 2018-02-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob03009f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Efficient, one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary spirocenters and three adjacent cycles in excellent yields and diastereoselectivities under mild conditions. Abstract : A novel and diastereoselective [3 + 2] annulation of isoindigos and Morita–Baylis–Hillman carbonates has been developed for the highly efficient and one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary spirocenters and three adjacent cycles in excellent yields (up to >99%) and diastereoselectivities (up to >20 : 1) under mild conditions within a few minutes. A series of dispiro[cyclopent-3′-ene]bisoxindoles were obtained and scale-up experiment was conducted with excellent results demonstrating the potential applications of this protocol.