Yb(OTf)3 catalyzed [1, 3]-rearrangement of 3-alkenyl oxindoles. Issue 1 (7th December 2021)

• Record Type: Journal Article
• Authors: Wu, Chaofei; Wan, Junlin; Song, Chao; He, Lingchen; Liu, Hongxin; Li, Xinhua; Li, Juan; Hu, Xin-Gen; Xiao, Hong-Ping; Jiang, Jun
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 1(2021)
• Page Start: 122
• Page End: 126
• Publication Date: 2021-12-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob02032j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient Yb(OTf)3 catalyzed [1, 3]-rearrangement of 3-alkenyl oxindoles was developed, affording diverse 3-ylideneoxindoles in good yield and Z / E selectivity. Besides, a one pot, sequential catalytic version was also achieved under mild condition. Abstract : A Yb(OTf)3 catalyzed [1, 3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields and Z / E selectivities (64%–89% yield, 78 : 22–>99 : 1 Z / E ). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1, 3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.