Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides1. Issue 34 (24th August 2017)

• Record Type: Journal Article
• Authors: Wang, Yafeng; Huang, Guanxin; Hu, Sha; Jin, Kaijun; Wu, Yan; Chen, Fener
• Is Part Of: Tetrahedron. Volume 73:Issue 34(2017)
• Page Start: 5055
• Page End: 5062
• Publication Date: 2017-08-24
• Subjects: Chloramphenicol base-sulfonamides catalysts -- Aldol reaction -- Asymmetric catalysis -- Chiral β-hydroxy thioesters; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.05.066
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A highly enantioselective synthesis of chiral β -hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting chiral β -hydroxy thioesters were obtained in high yields (up to 82%) with good to excellent enantioselectivities (up to 94% ee). The synthetic application of the methodology is illustrated by the asymmetric synthesis of the selective serotonin reuptake inhibitor dapoxetine. Graphical abstract: