A novel chiral DMAP–thiourea bifunctional catalyst catalyzed enantioselective Steglich and Black rearrangement reactions. Issue 15 (25th June 2019)

• Record Type: Journal Article
• Authors: Li, Qing-Hua; Zhang, Gui-Shan; Wang, Yu-Hui; Mei, Ming-Shun; Wang, Xin; Liu, Qiang; Yang, Xiao-Di; Tian, Ping; Lin, Guo-Qiang
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 15(2019)
• Page Start: 2624
• Page End: 2629
• Publication Date: 2019-06-25
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00691e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel chiral DMAP–thiourea bifunctional catalyst has been prepared and applied in the highly enantioselective Steglich and Black rearrangement reactions. Abstract : The first novel and efficient chiral DMAP–thiourea bifunctional catalyst has been successfully developed and applied in highly enantioselective acyl-transfer reactions. A series of 1, 3-oxazolyl carbonates are efficiently transformed to C -carboxyazlactones (Steglich rearrangement) by employing 5 mol% of this bifunctional nucleophilic catalyst with good yields and excellent enantioselectivities (up to 90% yield and 97% ee), and 2-benzofuranylcarbonates are also converted to 3, 3-disubstituted benzofuran-2-ones (Black rearrangement) with satisfactory asymmetric induction (up to 92% yield and 87% ee).