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Volumn 46, Issue 51, 2005, Pages 8941-8944

Enantioselective nucleophilic addition to N-(2-pyridylsulfonyl)imines by use of dynamically induced chirality

Author keywords

2 Pyridylsulfonyl group; Grignard reagents; Imine; Stereocontroller

Indexed keywords

IMINE; LEWIS ACID; NITROGEN; PYRIDINE DERIVATIVE;

EID: 27944445486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.085     Document Type: Article
Times cited : (28)

References (64)
  • 3
    • 0038106171 scopus 로고    scopus 로고
    • R. Bloch Chem. Rev. 98 1998 1407 1438
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 35
    • 2342524714 scopus 로고    scopus 로고
    • We have reported highly enantioselective radical addition to vinylsulfones, in which a chiral Lewis acid selectively coordinates one of the enantiotopic sulfonyl oxygens and nitrogen in the heteroarylsulfonyl group: H. Sugimoto, S. Nakamura, Y. Watanabe, and T. Toru Tetrahedron: Asymmetry 14 2003 3045 3055
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3045-3055
    • Sugimoto, H.1    Nakamura, S.2    Watanabe, Y.3    Toru, T.4
  • 42
    • 27944489875 scopus 로고    scopus 로고
    • note
    • The reaction of 1a with a catalytic amount (0.3 equiv) of bis(oxazoline) 3 and MeMgBr gave 2a with 29% ee.
  • 43
    • 27944465220 scopus 로고    scopus 로고
    • note
    • 2 afforded (S)-2a with 99% ee.
  • 46
    • 0035215207 scopus 로고    scopus 로고
    • Generally, the reactivity of Grignard reagents to imines is low: S. Saito, K. Hatanaka, and H. Yamamoto Synlett 2001 1859 1861
    • (2001) Synlett , pp. 1859-1861
    • Saito, S.1    Hatanaka, K.2    Yamamoto, H.3
  • 52
    • 0002829653 scopus 로고    scopus 로고
    • Conversion to N-alkyl-N-sulfonyl compounds or N-Boc-N-sulfonyl compounds prior to the cleavage is needed for removal of a tosyl group from the primary amines, see: B. Nyasse, L. Grehn, and U. Ragnarsson Chem. Commun. 1997 1017 1018 and references cited therein
    • (1997) Chem. Commun. , pp. 1017-1018
    • Nyasse, B.1    Grehn, L.2    Ragnarsson, U.3
  • 56
    • 27944459973 scopus 로고    scopus 로고
    • note
    • 2 at room temperature. This amide was found to be 99% ee by HPLC analysis using CHIRALCEL OD-H.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.