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Volumn 62, Issue 24, 1997, Pages 8560-8564

Preparation of Enantiopure 2,2,5,5-Tetramethyl-3,4-hexanediol and Its Use in Catalytic Enantioselective Oxidation of Sulfides to Sulfoxides

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EID: 0000979363     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971004y     Document Type: Article
Times cited : (84)

References (49)
  • 5
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    • In the past, the optically active diol 1 was prepared by the Sharpless osmium-catalyzed asymmetric dihydroxylation of (E)-2,2,5,5-tetramethyl-3-hexene (86%, 62% ee). Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4263
    • Ihentges, S.G.1    Sharpless, K.B.2
  • 9
    • 1542688640 scopus 로고
    • Optical Resolution Procedures for Chemical Compounds
    • Optical Resolution Information Center: New York
    • (a) Newman, P. Optical Resolution Procedures for Chemical Compounds. Alcohols, Phenols, Thiols, Aldehydes and Ketones; Optical Resolution Information Center: New York, 1984; Vol. 3.
    • (1984) Alcohols, Phenols, Thiols, Aldehydes and Ketones , vol.3
    • Newman, P.1
  • 19
    • 85077702395 scopus 로고
    • For some reviews on the synthesis and application of chiral sulfoxide, see: (a) Solladie, G. Synthesis 1981, 185. (b) Andersen, K. K. in The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley and Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 55-94. Posner, G. H. Ibid. Chapter 16, pp 823-849.
    • (1981) Synthesis , pp. 185
    • Solladie, G.1
  • 20
    • 0000825564 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley and Sons, Ltd.: Chichester, England, Chapter 3
    • For some reviews on the synthesis and application of chiral sulfoxide, see: (a) Solladie, G. Synthesis 1981, 185. (b) Andersen, K. K. in The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley and Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 55-94. Posner, G. H. Ibid. Chapter 16, pp 823-849.
    • (1988) The Chemistry of Sulfones and Sulfoxides , pp. 55-94
    • Andersen, K.K.1
  • 21
    • 0004178192 scopus 로고    scopus 로고
    • Chapter 16
    • For some reviews on the synthesis and application of chiral sulfoxide, see: (a) Solladie, G. Synthesis 1981, 185. (b) Andersen, K. K. in The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley and Sons, Ltd.: Chichester, England, 1988; Chapter 3, pp 55-94. Posner, G. H. Ibid. Chapter 16, pp 823-849.
    • The Chemistry of Sulfones and Sulfoxides , pp. 823-849
    • Posner, G.H.1
  • 22
    • 0001936441 scopus 로고
    • Asymmetric Oxidation of Sulfides
    • Ojima, I., Ed.; VCH: New York, References cited therein
    • (a) Kagan, H. B. Asymmetric Oxidation of Sulfides. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, pp 203-226. References cited therein,
    • (1993) Catalytic Asymmetric Synthesis , pp. 203-226
    • Kagan, H.B.1
  • 45
    • 85050296727 scopus 로고
    • Kinetic Resolution
    • Allinger, N. L., Eliel, E. L., Eds.; Interscience: New York
    • (a) Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Interscience: New York, 1987; Vol. 14, p 249.
    • (1987) Topics in Stereochemistry , vol.14 , pp. 249
    • Kagan, H.B.1    Fiaud, J.C.2
  • 48
    • 85034481276 scopus 로고    scopus 로고
    • note
    • The mother solution was concentrated under reduced pressure, and the residue was dissolved in hot MeOH. The solution was seeded with optically pure diastereopure 3 (ca. 20 mg), which was obtained by preparative HPLC (ODS) using MeOH as the eluent. It was kept overnight at room temperature to give 4.5 g of diastereomer 3 as colorless plates.
  • 49
    • 85034484228 scopus 로고    scopus 로고
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.