메뉴 건너뛰기




Volumn 72, Issue 14, 2007, Pages 5403-5406

trans-(±)-2-tert-butyl-3-phenyloxaziridine: A unique reagent for the oxidation of thiolates into sulfenates

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC THIOLATES; ORGANIC CHEMISTRY; OXIDIZING AGENTS; SULFOXIDES;

EID: 34447316415     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070700n     Document Type: Article
Times cited : (23)

References (66)
  • 8
    • 0001209715 scopus 로고    scopus 로고
    • Perfluorinated oxaziridines: (a) Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809-1824.
    • Perfluorinated oxaziridines: (a) Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809-1824.
  • 9
    • 27644563193 scopus 로고    scopus 로고
    • Alkoxysulfonyl oxaziridines: (b) Brodsky, B. H.; Du Bois, J. J. Am. Chem. Soc. 2005, 127, 15391-15393.
    • Alkoxysulfonyl oxaziridines: (b) Brodsky, B. H.; Du Bois, J. J. Am. Chem. Soc. 2005, 127, 15391-15393.
  • 10
    • 0035962966 scopus 로고    scopus 로고
    • Related oxaziridinium salts: (c) Poisson, D.; Cure, G.; Solladié, G.; Hanquet, G. Tetrahedron Lett. 2001, 42, 3745-3748.
    • Related oxaziridinium salts: (c) Poisson, D.; Cure, G.; Solladié, G.; Hanquet, G. Tetrahedron Lett. 2001, 42, 3745-3748.
  • 13
  • 14
    • 0011694235 scopus 로고
    • Oxygen-Transfer Reactions of Oxaziridines
    • Baumstark, A. L, Ed, JAI Press, Inc, Greenwich
    • (b) Davis, F. A.; Haque, M. S. Oxygen-Transfer Reactions of Oxaziridines. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press, Inc.: Greenwich 1990; Vol. 2, pp 61-116.
    • (1990) Advances in Oxygenated Processes , vol.2 , pp. 61-116
    • Davis, F.A.1    Haque, M.S.2
  • 16
    • 3142684447 scopus 로고    scopus 로고
    • The oxidation of thiolates into sulfenates is not a common reaction in organic synthesis: (a) O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183-211.
    • The oxidation of thiolates into sulfenates is not a common reaction in organic synthesis: (a) O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183-211.
  • 17
    • 3242712276 scopus 로고    scopus 로고
    • In contrast, this reaction is more encountered in biology, especially with processes involving cysteine residues: (b) Forman, H. J.; Fukuto, J. M.; Torres, M. Am. J. Physiol. Cell. Physiol. 2004, 287, C246-C256.
    • In contrast, this reaction is more encountered in biology, especially with processes involving cysteine residues: (b) Forman, H. J.; Fukuto, J. M.; Torres, M. Am. J. Physiol. Cell. Physiol. 2004, 287, C246-C256.
  • 23
    • 17044413284 scopus 로고    scopus 로고
    • Alternative routes to sulfenate species consist of manipulation of sulfoxides possessing an appropriate functionality, the most relevant contributions being the oxidative cleavage of 1-alkynyl sulfoxides with a Pd(0)-catalyst followed by transmetalation with Et2Zn, an addition/elimination methodology with β-sulfinylacrylates, a retro-Michael reaction initiated by a base from β-sulfinyl esters, and finally, the fluoride-mediated deprotection of 2-(trimethylsilyl)ethyl sulfoxides. See ref 5a and: (a) Caupène, C, Boudou, C, Perrio, S, Metzner, P. J. Org. Chem. 2005, 70, 2812-2815
    • 2Zn, an addition/elimination methodology with β-sulfinylacrylates, a retro-Michael reaction initiated by a base from β-sulfinyl esters, and finally, the fluoride-mediated deprotection of 2-(trimethylsilyl)ethyl sulfoxides. See ref 5a and: (a) Caupène, C.; Boudou, C.; Perrio, S.; Metzner, P. J. Org. Chem. 2005, 70, 2812-2815.
  • 27
    • 0000449359 scopus 로고    scopus 로고
    • We previously reported that the outcome of the oxidation reaction with aromatic thiolates highly depends on the oxaziridine structure: Sandrinelli, F, Perrio, S, Beslin, P. Org. Lett. 1999, 1, 1177-1180
    • We previously reported that the outcome of the oxidation reaction with aromatic thiolates highly depends on the oxaziridine structure: Sandrinelli, F.; Perrio, S.; Beslin, P. Org. Lett. 1999, 1, 1177-1180.
  • 28
    • 0001414645 scopus 로고    scopus 로고
    • Sulfenate salts, whose structure contains an unshared electron pair adjacent to the sulfur center, are considered as α-nucleophiles with an exalted reactivity. As a direct consequence, the double oxidation reaction leading to the sulfinate is generally preferred: Kice, J. L.; Cleveland, J. P. J. Am. Chem. Soc. 1973, 95, 104-109.
    • Sulfenate salts, whose structure contains an unshared electron pair adjacent to the sulfur center, are considered as α-nucleophiles with an exalted reactivity. As a direct consequence, the double oxidation reaction leading to the sulfinate is generally preferred: Kice, J. L.; Cleveland, J. P. J. Am. Chem. Soc. 1973, 95, 104-109.
  • 35
    • 0010330326 scopus 로고    scopus 로고
    • The reaction of this type of reagent with lithium and Grignard reagent, lithium amide bases and potassium phenolates, proceeds probably with an initial electron-transfer mechanism: (c) Davis, F. A.; Mancinelli, P. A.; Balasubramanian, K.; Nadir, U. K. J. Am. Chem. Soc. 1979, 101, 1044-1045.
    • The reaction of this type of reagent with lithium and Grignard reagent, lithium amide bases and potassium phenolates, proceeds probably with an initial electron-transfer mechanism: (c) Davis, F. A.; Mancinelli, P. A.; Balasubramanian, K.; Nadir, U. K. J. Am. Chem. Soc. 1979, 101, 1044-1045.
  • 41
    • 3142710052 scopus 로고    scopus 로고
    • A single isomer, probably with an E configuration, is obtained: (a) Lipshutz, B. H.; Shimizu, H. Angew. Chem., Int. Ed. Engl. 2004, 43, 2228-2230.
    • A single isomer, probably with an E configuration, is obtained: (a) Lipshutz, B. H.; Shimizu, H. Angew. Chem., Int. Ed. Engl. 2004, 43, 2228-2230.
  • 47
    • 20444463151 scopus 로고    scopus 로고
    • This is particularly the case with those with α-enolizable protons: (a) Desrosiers, J.-N, Côté, A, Charette, A. B. Tetrahedron 2005, 61, 6186-6192
    • This is particularly the case with those with α-enolizable protons: (a) Desrosiers, J.-N.; Côté, A.; Charette, A. B. Tetrahedron 2005, 61, 6186-6192.
  • 52
    • 34447335475 scopus 로고    scopus 로고
    • 1H NMR spectroscopy. As a single equivalent of oxidant was employed, sulfinate formation implied systematically the presence of unreacted thiolate, which upon the electrophilic quench was readily converted in situ into the corresponding thioether.
    • 1H NMR spectroscopy. As a single equivalent of oxidant was employed, sulfinate formation implied systematically the presence of unreacted thiolate, which upon the electrophilic quench was readily converted in situ into the corresponding thioether.
  • 54
    • 0020765317 scopus 로고    scopus 로고
    • When an excess of n-BuLi was introduced, benzylated imine 6 was detected. Its formation was interpreted by hydrogen abstraction on the methyl substituent of the liberated imine 4b, followed by C-alkylation of the resulting azaallyl anion. As a checking experiment, direct reaction with 4b in the presence of a stoichiometric amount of base furnished 6 in 40% yield. For precedents with other imines, see: (a) Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. J. Am. Chem. Soc. 1983, 105, 4396-4400.
    • When an excess of n-BuLi was introduced, benzylated imine 6 was detected. Its formation was interpreted by hydrogen abstraction on the methyl substituent of the liberated imine 4b, followed by C-alkylation of the resulting azaallyl anion. As a checking experiment, direct reaction with 4b in the presence of a stoichiometric amount of base furnished 6 in 40% yield. For precedents with other imines, see: (a) Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. J. Am. Chem. Soc. 1983, 105, 4396-4400.
  • 58
    • 34447297431 scopus 로고    scopus 로고
    • Emmons, W. D.; Pagano, A. S. Organic Syntheses; Wiley: New York, 1973; Collect. V, pp 191-193.
    • (b) Emmons, W. D.; Pagano, A. S. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, pp 191-193.
  • 59
    • 37049137779 scopus 로고    scopus 로고
    • Aldimines 4d-e were produced completely in the E configuration: (a) Bjørgo, J.; Boyd, D. R.; Watson, C. G.; Jennings, W. B.; Jerina, D. M. J. Chem. Soc., Perkin Trans. 2 1974, 1081-1084.
    • Aldimines 4d-e were produced completely in the E configuration: (a) Bjørgo, J.; Boyd, D. R.; Watson, C. G.; Jennings, W. B.; Jerina, D. M. J. Chem. Soc., Perkin Trans. 2 1974, 1081-1084.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.