Enantioselective synthesis of chiral 3-alkyl-3-nitro-4-chromanones via chiral thiourea-catalysed intramolecular Michael-type cyclization. Issue 34 (13th August 2021)

• Record Type: Journal Article
• Authors: Chen, Huiqing; Tang, Jie; Liu, Ting; Yu, Li-Fang; Xing, Dong; Yang, Fan
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 34(2021)
• Page Start: 7403
• Page End: 7408
• Publication Date: 2021-08-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01296g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The enantioselective synthesis of chiral 3-alkyl-3-nitro-4-chromanones is realized via a chiral thiourea-catalysed intramolecular Michael-type cyclization reaction. Abstract : Herein we report an enantioselective method for the rapid construction of chiral 3-nitro-4-chromanones via a chiral thiourea-catalyzed intramolecular Michael-type cyclization reaction. With this method, a series of 3, 3-disubstituted-3-nitro-4-chromanones bearing contiguous C2/C3 stereocenters were obtained with high diastereoselectivities and good to excellent enantioselectivities. In vitro biological evaluations indicated that the chiral amide derivative of the product showed more potent antitumor activities than both the racemic and the corresponding enantiomers, showcasing the high influence of enantioselective methodology development toward medicinal studies.