Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates. (March 2017)

• Record Type: Journal Article
• Authors: Jiang, Lin; Li, Yong-Gen; Li, Hang; Yuan, Ming-Wei; Chuan, Yong-Ming; Li, Hong-Li; Yuan, Ming-Long
• Is Part Of: Journal of chemical research. Volume 41:Number 3(2017)
• Page Start: 160
• Page End: 164
• Publication Date: 2017-03
• Subjects: Morita–Baylis–Hillman carbonate -- 3-alkenyloxindole -- allylic substitution -- sulfinate -- isatin; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751917X14878812592652
• Languages: English
• ISSNs: 1747-5198

Abstract

A variety of biologically and synthetically useful 3-alkenyloxindoles were rapidly synthesised via an SN 2′-type allylic substitution reaction of isatin-derived Morita–Baylis–Hillman carbonates with sodium sulfinates. The syntheses were conducted under catalyst-free reaction conditions and good to excellent product yields (up to 96%) and Z/E selectivities (up to >20:1) were obtained.