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Volumn 69, Issue 20, 2004, Pages 6916-6919

Highly chemoselective oxidation of dithioester enethiolates to sulfenates: Application to the synthesis of ketene dithioacetal S-oxides

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; DERIVATIVES; HALOGEN COMPOUNDS; OLEFINS; OXIDATION; VINYL RESINS;

EID: 4644287287     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0492362     Document Type: Article
Times cited : (23)

References (75)
  • 47
    • 0041702197 scopus 로고    scopus 로고
    • (b) Sandrinelli, F.; Perrio, S.; Averbuch-Pouchot, M.-T. Org. Lett. 2002, 4, 3619-3622. For a very recently published review on sulfenate salts, see: O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183-211.
    • (2002) Org. Lett. , vol.4 , pp. 3619-3622
    • Sandrinelli, F.1    Perrio, S.2    Averbuch-Pouchot, M.-T.3
  • 48
    • 3142684447 scopus 로고    scopus 로고
    • (b) Sandrinelli, F.; Perrio, S.; Averbuch-Pouchot, M.-T. Org. Lett. 2002, 4, 3619-3622. For a very recently published review on sulfenate salts, see: O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183-211.
    • (2004) J. Sulfur Chem. , vol.25 , pp. 183-211
    • O'Donnell, J.S.1    Schwan, A.L.2
  • 49
    • 0002754433 scopus 로고
    • With the exception of our work, there is only one reported example of the use of oxaziridine 1a (hydroxylation of a β-lactam). Shimizu, M.; Ishida, T.; Fujisawa, T. Chem. Lett. 1994, 1403-1406.
    • (1994) Chem. Lett. , pp. 1403-1406
    • Shimizu, M.1    Ishida, T.2    Fujisawa, T.3
  • 54
    • 0001311326 scopus 로고
    • 1 groups located on the same side of the C=C bond). Beslin, P.; Vallée, Y. Tetrahedron 1985, 41, 2691-2705. In contrast, the analogous carbonyl compounds afford trans enolates under similar kinetic conditions.
    • (1985) Tetrahedron , vol.41 , pp. 2691-2705
    • Beslin, P.1    Vallée, Y.2
  • 56
    • 84982480964 scopus 로고    scopus 로고
    • For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
    • (1976) Bull. Soc. Chim. Belg. , vol.85 , pp. 431-434
    • Poupaert, J.1    Bruylants, A.2
  • 57
    • 0026317480 scopus 로고
    • For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
    • (1991) Biochem. Biophys. Res. Commun. , vol.181 , pp. 657-663
    • Li, J.1    Guha, K.2    Creighton, D.J.3
  • 58
    • 84982480964 scopus 로고    scopus 로고
    • German (East) Patent 86823, 1973
    • For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
    • Scheithauer, S.1
  • 59
    • 4644270477 scopus 로고    scopus 로고
    • note
    • The imine byproduct of the oxidation reaction undergoes hydrolytic cleavage to benzenesulfonamide and the volatile pinacolone.
  • 60
    • 4644346273 scopus 로고    scopus 로고
    • note
    • 2 protons (see the Supporting Information).
  • 61
    • 4644260760 scopus 로고
    • 1H NMR data of the pair of (Z) and (E) isomers. The vinylic proton in the (Z) series occurs at approximately δ 6.3 ppm but is substantially deshielded at around 6.8 ppm in the corresponding (E) isomer, (a) Cazes, B.; Huynh, C.; Julia, S.; Ratovelomanana, V.; Ruel, O. J. Chem. Res. (M) 1978, 957-968. (b) Seebach, D.; Bürstinghaus, R.; Gröbel, B.-T.; Kolb, M. Liebigs. Ann. Chem. 1977, 830-845.
    • (1978) J. Chem. Res. (M) , pp. 957-968
    • Cazes, B.1    Huynh, C.2    Julia, S.3    Ratovelomanana, V.4    Ruel, O.5
  • 62
    • 84981450407 scopus 로고
    • 1H NMR data of the pair of (Z) and (E) isomers. The vinylic proton in the (Z) series occurs at approximately δ 6.3 ppm but is substantially deshielded at around 6.8 ppm in the corresponding (E) isomer, (a) Cazes, B.; Huynh, C.; Julia, S.; Ratovelomanana, V.; Ruel, O. J. Chem. Res. (M) 1978, 957-968. (b) Seebach, D.; Bürstinghaus, R.; Gröbel, B.-T.; Kolb, M. Liebigs. Ann. Chem. 1977, 830-845.
    • (1977) Liebigs. Ann. Chem. , pp. 830-845
    • Seebach, D.1    Bürstinghaus, R.2    Gröbel, B.-T.3    Kolb, M.4
  • 63
    • 0028087642 scopus 로고
    • 2. See the Supporting Information. (a) Dannhardt, G.; Kiefer, W. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 509-514. (b) Mazzanti, G.; van Helvoirt, E.; van Vliet, L. A.; Ruinaard, R.; Masiero, S.; Bonini, B. F.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1994, 3299-3304. (c) Schwan, A. L.; Roche, M. R.; Gallagher, J. F.; Ferguson, G. Can. J. Chem. 1994, 72, 312-324.
    • (1994) Arch. Pharm. (Weinheim, Ger.) , vol.327 , pp. 509-514
  • 65
    • 0005003154 scopus 로고
    • 2. See the Supporting Information. (a) Dannhardt, G.; Kiefer, W. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 509-514. (b) Mazzanti, G.; van Helvoirt, E.; van Vliet, L. A.; Ruinaard, R.; Masiero, S.; Bonini, B. F.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1994, 3299-3304. (c) Schwan, A. L.; Roche, M. R.; Gallagher, J. F.; Ferguson, G. Can. J. Chem. 1994, 72, 312-324.
    • (1994) Can. J. Chem. , vol.72 , pp. 312-324
    • Schwan, A.L.1    Roche, M.R.2    Gallagher, J.F.3    Ferguson, G.4
  • 66
    • 4644331056 scopus 로고    scopus 로고
    • note
    • 2O, Claisen rearrangement into a sulfine, and finally rearrangement, via an oxathiirane, with loss of elemental sulfur (see the Supporting Information).
  • 67
    • 4644361254 scopus 로고    scopus 로고
    • note
    • 1, which has a phenyl substituent, a 0.7 ppm downfield shift is observed for the vinylic proton, but the singlet for the (Z) isomer again occurs at higher field (δ 7.00 against 7.63 ppm).
  • 69
    • 4644270954 scopus 로고    scopus 로고
    • note
    • The relative configuration was not determined.
  • 71
    • 4644373283 scopus 로고    scopus 로고
    • note
    • The yield is calculated from the dithioester based on an optimum value of 50%, as a single equivalent of oxidant is used.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.