Remote asymmetric conjugate addition catalyzed by a bifunctional spiro-pyrrolidine-derived thiourea catalyst. Issue 13 (23rd April 2021)

• Record Type: Journal Article
• Authors: Xu, Ming-Hui; Yuan, Yong-Hai; Liang, Dong-Dong; Zhang, Xiao-Ming; Zhang, Fu-Min; Tu, Yong-Qiang; Ma, Ai-Jun; Zhang, Kun; Peng, Jin-Bao
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 13(2021)
• Page Start: 3292
• Page End: 3297
• Publication Date: 2021-04-23
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00238d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel spiro-pyrrolidine (SPD)-derived bifunctional thiourea catalyst has been developed and used in a stereoselective conjugate addition of furfurals to β, γ-unsaturated α-ketoesters. Abstract : A novel spiro-pyrrolidine (SPD)-derived bifunctional thiourea catalyst has been developed, enabling the development of a stereoselective conjugate addition of furfurals to β, γ-unsaturated α-ketoesters. The reaction represents an example of asymmetric trienamine catalysis in the benzylic C–H functionalization of 5-benzylfurfurals, and the rigid spirocyclic framework of the catalyst is proven to be essential for a highly enantioselective transformation.