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
(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...
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| Published in | European journal of organic chemistry Vol. 2016; no. 5; pp. 906 - 909 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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01.02.2016
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| Abstract | (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. |
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| AbstractList | (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. (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 [alpha],[beta]-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. |
| Author | Liu, Qinghe Hu, Jinbo Shen, Xiao Zhang, Wei |
| Author_xml | – sequence: 1 givenname: Xiao orcidid: 0000-0002-8675-1213 surname: Shen fullname: Shen, Xiao organization: Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China – sequence: 2 givenname: Qinghe orcidid: 0000-0003-3125-7135 surname: Liu fullname: Liu, Qinghe organization: Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China – sequence: 3 givenname: Wei surname: Zhang fullname: Zhang, Wei organization: Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China – sequence: 4 givenname: Jinbo surname: Hu fullname: Hu, Jinbo email: jinbohu@sioc.ac.cn organization: Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China |
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| Keywords | 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 |
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| Snippet | (Sulfonimidoyl)cyclopropanes have become the subject of special interest since they combine the advantages of two chemical leads (cyclopropane and... |
| Source | Web of Science |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | 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 |
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