Catalyst-free synthesis of 2, 3-dihydrobenzofurans through [4+1] cycloaddition of ortho-hydroxyphenylsubstituted para-quinone methides and sulfur ylides. Issue 5 (1st February 2018)

• Record Type: Journal Article
• Authors: Chen, Xin-Meng; Xie, Ke-Xin; Yue, Deng-Feng; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng
• Is Part Of: Tetrahedron. Volume 74:Issue 5(2018)
• Page Start: 600
• Page End: 605
• Publication Date: 2018-02-01
• Subjects: para-Quinone methides -- Sulfur yildes -- 2, 3-Dihydrobenzofurans -- Catalyst-free -- Cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.12.038
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient [4+1] cycloaddition of ortho -hydroxyphenylsubstituted para- quinone methides and sulfur ylides was achieved under the catalyst-free condition. With this developed protocol, a series of trans -2, 3-dihydrobenzofurans were obtained in excellent yields (up to 99%) with high diastereoselectivities (>20:1 dr). The usefulness of the protocol was also demonstrated by the versatile conversions of the 2, 3-dihydrobenzofurans into other functionalized benzofurans. Graphical abstract: