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Volumn 46, Issue 33, 2005, Pages 5555-5558

Asymmetric synthesis of 1-substituted-1-(pyridin-2-yl)methylamines by diastereoselective reduction of enantiopure N-p-toluenesulfinyl ketimines

Author keywords

Diastereoselective reduction; N p Toluenesulfinyl ketimines; Nitrogen heterocycles; Pyridyl amines

Indexed keywords

IMINE; KETONE DERIVATIVE; METHYLAMINE; PYRIDINE DERIVATIVE; SULFUR DERIVATIVE; TOLUENE DERIVATIVE;

EID: 22144433753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.019     Document Type: Article
Times cited : (23)

References (21)
  • 6
    • 0027403567 scopus 로고
    • 4) of the chiral auxiliary, the 2-cyclohexyl-1-(pyridin-2-yl)ethylamine was obtained with good enantiomeric excess (80-96%). However, the yield of the last step was low (35-40%) C.K. Miao, R. Sorcek, and P.-J. Jones Tetrahedron Lett. 34 1993 2259
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2259
    • Miao, C.K.1    Sorcek, R.2    Jones, P.-J.3
  • 7
    • 0001084241 scopus 로고    scopus 로고
    • Syntheses and Reactions of Sulfinimines
    • C.M. Raynor JAl Press Stanford, CT
    • For a recent review, see: P. Zhou, B.-C. Chen, and F.A. Davis Syntheses and Reactions of Sulfinimines C.M. Raynor Advances in Sulfur Chemistry Vol. 2 2000 JAl Press Stanford, CT 249 282
    • (2000) Advances in Sulfur Chemistry , vol.2 , pp. 249-282
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 8
    • 0036851670 scopus 로고    scopus 로고
    • Another very attractive N-substituent is the tert-butyl sulfinyl group, however the enantiopure tert-butanesulfinamide is much more expensive than the (S)-(+)-p-toluenesulfinamide, therefore starting our investigation, we decided to use the latter. For a review on N-tert-butanesulfinyl imines, see: J.A. Ellman, T.D. Owens, and T.P. Tang Acc. Chem. Res. 35 2002 984
    • (2002) Acc. Chem. Res. , vol.35 , pp. 984
    • Ellman, J.A.1    Owens, T.D.2    Tang, T.P.3
  • 14
    • 32744467803 scopus 로고    scopus 로고
    • note
    • 2OS: C, 64.58; H, 6.19; N, 10.76. Found: C, 63.86; H, 6.42; N, 10.65.
  • 15
    • 32744473992 scopus 로고    scopus 로고
    • note
    • S,S)-5a (40.0 mg, 77%).
  • 16
    • 32744474129 scopus 로고    scopus 로고
    • note
    • S,S)-5a (46.8 mg, 90%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.