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Volumn 50, Issue 26, 2009, Pages 3482-3484

The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Author keywords

Cleavage; Deprotection; Dynamic kinetic resolution; Ellman's auxiliary; Sulfinimines; tert Butylsulfinamide

Indexed keywords

ALCOHOL; AMMONIA; CHLORIDE; SULFINAMIDE; SULFINIC ACID DERIVATIVE;

EID: 65549159759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.020     Document Type: Article
Times cited : (44)

References (36)
  • 14
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    • 2O in an NMR study but it was not isolated:
    • 2O in an NMR study but it was not isolated:. Brinner K.M., and Ellman J.A. Org. Biomol. Chem. 3 (2005) 2109-2113
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 2109-2113
    • Brinner, K.M.1    Ellman, J.A.2
  • 15
    • 0141683733 scopus 로고    scopus 로고
    • 4Cl as an additive for auxiliary cleavage by acidic resins and MeOH, and suggested it was effective due to attack of chloride at sulfur:
    • 4Cl as an additive for auxiliary cleavage by acidic resins and MeOH, and suggested it was effective due to attack of chloride at sulfur:. Mukade T., Dragoli D.R., and Ellman J.A. J. Comb. Chem. 5 (2003) 590-596
    • (2003) J. Comb. Chem. , vol.5 , pp. 590-596
    • Mukade, T.1    Dragoli, D.R.2    Ellman, J.A.3
  • 18
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    • note
    • 2 returned starting material.
  • 26
    • 0033551894 scopus 로고    scopus 로고
    • 2O gave a dr of 91:9 and 66% yield after 3 days. They attributed the low yield to trapping of 8 as its HCl salt but noted that added base had a limited effect on yield and dr. They also noted that there was little effect of solvent on diastereocontrol:
    • 2O gave a dr of 91:9 and 66% yield after 3 days. They attributed the low yield to trapping of 8 as its HCl salt but noted that added base had a limited effect on yield and dr. They also noted that there was little effect of solvent on diastereocontrol:. Drabowicz J., Bujnicki B., Biscarini P., Mikolajczyk M. Tetrahedron: Asymmetry 10 (1999) 3177-3187
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 3177-3187
    • Drabowicz, J.1    Bujnicki, B.2    Biscarini, P.3    Mikolajczyk, M.4
  • 32
    • 0028875576 scopus 로고
    • For capture of the p-toluenesulfinyl auxiliary with menthol followed by cycles of fractional crystallization and epimerization see:
    • For capture of the p-toluenesulfinyl auxiliary with menthol followed by cycles of fractional crystallization and epimerization see:. Davis F.A., Reddy R.E., and Szewczyk J.M. J. Org. Chem. 60 (1995) 7037-7039
    • (1995) J. Org. Chem. , vol.60 , pp. 7037-7039
    • Davis, F.A.1    Reddy, R.E.2    Szewczyk, J.M.3
  • 36
    • 65549136407 scopus 로고    scopus 로고
    • note
    • The standard work-up uses MeOH/HCl which presumably traps the sulfinyl chloride as methyl tert-butylsulfinate ester.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.