Stereoselective Synthesis of (Sulfonimidoyl)cyclopropanes with (R)-PhSO(NTs)CH2Cl and α,β-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: Book Review
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2016; WILEY‐VCH Verlag
• Subjects: C-Cl bond cleavage; C-S bond cleavage; Cyclopropanation; Cyclopropane; Sulfoximine
• 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 α,β‐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. The first (sulfonimidoyl)cyclopropanation of α,β‐unsaturated carbonyl compounds with (R)‐PhSO(NTs)CH2Cl was achieved to afford optically enriched (sulfonimidoyl)cyclopropanes in good yields with excellent diastereoselectivities. The reaction shows a broad substrate scope. The Weinreb amide group and the counter cation of the base were found to be important for the selective C–Cl bond cleavage of the sulfoximine reagent.