Stereoselective Synthesis of (Sulfonimidoyl)cyclopropanes with (R)-PhSO(NTs)CH2Cl and ,-Unsaturated Weinreb Amides: Tuning the of Selectivity between C-Cl and C-S Bond Cleavage

• Published in: European journal of organic chemistry Vol. 2016; no. 5; pp. 906 - 909
• Main Authors: Shen, Xiao, Liu, Qinghe, Zhang, Wei, Hu, Jinbo
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.02.2016; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ORGANIC-SYNTHESIS; SUBSTITUTION; SULFOXIMINES; CYCLOPROPANES; C-Cl bond cleavage; ALPHA-FLUOROSULFOXIMINES; Cyclopropanation; C-S bond cleavage; Cyclopropane; Sulfoximine; MONOFLUOROALKENES; ARYL KETONES; NUCLEOPHILIC DIFLUOROMETHYLATION; DERIVATIVES; PHSO(NTBS)CF2H
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201501611

(Sulfonimidoyl)cyclopropanes have become the subject of special interest since they combine the advantages of two chemical leads (cyclopropane and sulfoximine). However, their synthesis is limited, and the stereoselective synthesis of optically enriched (sulfonimidoyl)cyclopropanes still remains an unsolved task. Here we report the first stereoselective (sulfonimidoyl)cyclopropanation reaction using ,-unsaturated Weinreb amides and (R)-PhSO(NTs)CH2Cl [(R)-1]. This reaction possesses a broad substrate scope, and the products can be easily transformed into other useful cyclopropyl-containing and/or sulfonimidoyl-containing compounds. The Weinreb amide group and the counter cation of the base were found to be important for the selective C-Cl bond cleavage.