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Volumn , Issue 41, 2008, Pages 5233-5235

Asymmetric synthesis of either diastereomer of trifluoromethylated allylic amines by the selective reduction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IMINE; SULFINAMIDE;

EID: 54949124261     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b810459j     Document Type: Article
Times cited : (54)

References (47)
  • 14
    • 0003907264 scopus 로고
    • J. T. Welch and S. Eshwarakrishman, Wiley, New York, NY
    • Fluorine in Bioorganic Chemistry, eds., J. T. Welch, and, S. Eshwarakrishman,, Wiley, New York, NY, 1991
    • (1991) Fluorine in Bioorganic Chemistry, Eds.
  • 24
    • 0037223313 scopus 로고    scopus 로고
    • 3-substituted N-tert-butylsulfinyl imines, see:
    • J. A. Ellman Pure Appl. Chem. 2003 75 39
    • (2003) Pure Appl. Chem. , vol.75 , pp. 39
    • Ellman, J.A.1
  • 36
    • 0030694323 scopus 로고    scopus 로고
    • To our knowledge only a single example has been reported for the reduction of α,β-unsaturated N-tert-butylsulfinyl ketoimines. See:
    • G. Liu D. A. Cogan J. A. Ellman J. Am. Chem. Soc. 1997 119 9913
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9913
    • Liu, G.1    Cogan, D.A.2    Ellman, J.A.3
  • 37
    • 0033543624 scopus 로고    scopus 로고
    • For the stereoselectivity reversal of N-tert-butylsulfinyl imines in hydride reduction, see:
    • G. Borg D. A. Cogan J. A. Ellman Tetrahedron Lett. 1999 40 6709
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6709
    • Borg, G.1    Cogan, D.A.2    Ellman, J.A.3
  • 41
    • 33845707628 scopus 로고    scopus 로고
    • The absolute configuration of product 3a was assigned by cleaving the sulfinamide with HCl and examining the optical rotation of the known salt. See ESI for details For HMPA used as Lewis base to improve the diastereoselectivity in additions to imines, see:
    • G. Chelucci S. Baldino S. Chessa G. A. Pinna F. Soccolini Tetrahedron: Asymmetry 2006 17 3163
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3163
    • Chelucci, G.1    Baldino, S.2    Chessa, S.3    Pinna, G.A.4    Soccolini, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.