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Volumn , Issue 11, 2003, Pages 1659-1662

Oxidative functionalisation of superquat enamides: Asymmetric synthesis of homochiral 1,2 diols

Author keywords

Asymmetric synthesis; Homochiral 1,2 diols; SuperQuat enamides

Indexed keywords

3 CHLOROBENZOIC ACID; 3 CHLOROPERBENZOIC ACID; 4 PHENYL 5,5 DIMETHYLOXAZOLIDINONE; AMIDE; DIMETHYLDIOXIRANE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0041409710     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41425     Document Type: Article
Times cited : (29)

References (40)
  • 21
    • 0043162879 scopus 로고    scopus 로고
    • DPhil Thesis; University of Oxford: UK
    • For preliminary studies in this area see: Sanganee, H. J. DPhil Thesis; University of Oxford: UK, 1996.
    • (1996)
    • Sanganee, H.J.1
  • 22
    • 0042662015 scopus 로고    scopus 로고
    • note
    • +).
  • 23
    • 0001068021 scopus 로고
    • (a) Based upon the related protocol for the synthesis of N-alkenyl lactams described in: Zezza, C. A.; Smith, M. B. Synth. Commun. 1987, 17, 729.
    • (1987) Synth. Commun. , vol.17 , pp. 729
    • Zezza, C.A.1    Smith, M.B.2
  • 26
    • 0043162880 scopus 로고    scopus 로고
    • note
    • + requires 488.1232.
  • 27
    • 0041660055 scopus 로고    scopus 로고
    • note
    • 2 = 0.059. Crystallographic data (excluding structure factors) has been deposited with the Cambridge Crystallographic Data Centre (CCDC 213199).
  • 28
    • 0037012929 scopus 로고    scopus 로고
    • For related N-acyliminium species see: (a) Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989. (b) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
    • (2002) J. Org. Chem. , vol.67 , pp. 2989
    • Marcantoni, E.1    Mecozzi, T.2    Petrini, M.3
  • 30
    • 0043162877 scopus 로고    scopus 로고
    • note
    • N2 opening of epoxide 7 at C(1′) would be expected to furnish anti-(4S, 1′S,2′S)-1′ -m-chlorobenzoate-20 (Scheme 5).
  • 31
    • 0042160977 scopus 로고    scopus 로고
    • note
    • 2], 2.88 and 2.48 (2 x 1 H, br s, OH).
  • 32
    • 0042160976 scopus 로고    scopus 로고
    • note
    • Commercially available from the Aldrich Chemical Company.
  • 34
    • 0042160986 scopus 로고    scopus 로고
    • note
    • Chiral gas chromatography of diol 10 was performed on a CE Instruments Trace GC (Thermoquest) machine with an SGE Cydex-β stationary phase (25 m x 0.22 mm) with helium as the carrier gas and a flow rate of 1.5 mL per min using a FID detector. An isocratic temperature of 40 °C was followed for 120 minutes, followed by a temperature ramp of 4 °C to 140 °C for 120 minutes and comparison with an authentic racemic sample. Retention times were 159.25 min (S) and 159.87 min (R).
  • 36
    • 0041660053 scopus 로고    scopus 로고
    • note
    • Chiral gas chromatography of the bis-trifluoroacetate derivative of 17 was performed on a CE Instruments Trace GC (Thermoquest) machine with an SGE Cydex-β stationary phase (25 m x 0.22 mm) with helium as the carrier gas and a flow rate of 2 mL per min using a FID detector. An isocratic temperature of 50 °C was followed for 120 minutes, followed by a temperature ramp of 4 °C to 110 °C for 60 minutes and comparison with an authentic racemic sample. Retention times were 139.38 min (S) and 139.89 min (R).
  • 38
    • 0041660051 scopus 로고    scopus 로고
    • note
    • Although chromatographic purification led to the separation of diol and auxiliary, the isolated yield of the diol could be increased by acetylation of the crude reaction mixture resulting from reduction, which facilitated chromatographic purification of the bis-acetate derivative of the diol.
  • 39
    • 0042160984 scopus 로고    scopus 로고
    • note
    • 2 51.00 (R) and 51.07 min (S).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.