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Volumn 45, Issue 33, 2006, Pages 5546-5549

Salt-free iridium-catalyzed asymmetric allylic animations with N,N-diacylamines and ortho-nosylamide as ammonia equivalents

Author keywords

Allylic amination; Enantioselectivity; Iridium; Pyrrolidines; Ring closing metathesis

Indexed keywords

AMINATION; AMINES; CATALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 33748639706     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601472     Document Type: Article
Times cited : (147)

References (42)
  • 25
    • 0036851670 scopus 로고    scopus 로고
    • For further asymmetric syntheses of amines with a stereogenic center in α-position to N see: a) J. A. Ellman, T. D. Owens, T. P. Tang, Acc. Chem. Res. 2002, 35, 984;
    • (2002) Acc. Chem. Res. , vol.35 , pp. 984
    • Ellman, J.A.1    Owens, T.D.2    Tang, T.P.3
  • 29
    • 77955911241 scopus 로고    scopus 로고
    • (Ed.: P. A. Evans), Wiley, New York
    • P. A. Evans et al. have prepared corresponding N-tosyl derivatives by stereoconservative Rh-catalyzed allylic substitution at enantioenriched derivatives of allylic alcohols, which does not constitute an asymmetric synthesis. Surveys: a) D. K. Leahy, P. A. Evans in Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley, New York, 2005, p. 191;
    • (2005) Modern Rhodium-Catalyzed Organic Reactions , pp. 191
    • Leahy, D.K.1    Evans, P.A.2
  • 31
    • 4043070494 scopus 로고    scopus 로고
    • The absolute configurations of the products described herein were as anticipated (Ref. [8]); for independent determinations see a) M. Atobe, N. Yamazaki, C. Kibayashi, J. Org. Chem. 2004, 69, 5595;
    • (2004) J. Org. Chem. , vol.69 , pp. 5595
    • Atobe, M.1    Yamazaki, N.2    Kibayashi, C.3
  • 33
    • 33748675398 scopus 로고    scopus 로고
    • note
    • For substrate 1a (in combination with L2) a reaction time of 2.5 h was required to give the substitution product in 87 % yield with 98% ee and a regioselectivity of 96:4.
  • 36
    • 0035804985 scopus 로고    scopus 로고
    • 2, which has previously been used in Pd-catalyzed allylic substitutions (Y. Wang, K. Ding, J. Org. Chem. 2001, 66, 3238).
    • (2001) J. Org. Chem. , vol.66 , pp. 3238
    • Wang, Y.1    Ding, K.2
  • 37
    • 84989431741 scopus 로고
    • To our knowledge, this compound has not been previously described. We prepared it according to a general procedure (Y. Lin, S. A. Lang, Jr, Synthesis 1980, 119) in 88% yield.
    • (1980) Synthesis , pp. 119
    • Lin, Y.1    Lang Jr., S.A.2
  • 41
    • 33748673473 scopus 로고    scopus 로고
    • note
    • The ee values of the free amines were determined and found to agree, within the range of precision, with those of the protected precursors.
  • 42
    • 1442360753 scopus 로고    scopus 로고
    • (Ed.: R. H. Grubbs), Wiley, New York
    • Handbook of Metathesis (Ed.: R. H. Grubbs), Wiley, New York, 2003.
    • (2003) Handbook of Metathesis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.