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Volumn 45, Issue 39, 2004, Pages 7235-7238

An amine sulfonamide organocatalyst for promoting direct, highly enantioselective α-aminoxylation reactions of aldehydes and ketones

Author keywords

Aldehydes; Asymmetric catalysis; Ketones; Pyrrolidine sulfonamide; Aminoxylation

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; KETONE DERIVATIVE; ORGANIC SOLVENT; PROLINE; SULFONAMIDE;

EID: 4444260494     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.029     Document Type: Article
Times cited : (103)

References (45)
  • 1
    • 0009506491 scopus 로고
    • G. Helmchen R.W. Hoffman J. Mulzer E. Schaumann Georg Thieme Stuttgart
    • Reviews of hydroxylation: F.A. Davis, and B.C. Chen G. Helmchen R.W. Hoffman J. Mulzer E. Schaumann Houben Weyl: Methods of Organic Chemistry Vol. E 21 1995 Georg Thieme Stuttgart 4497
    • (1995) Houben Weyl: Methods of Organic Chemistry , vol.21 , pp. 4497
    • Davis, F.A.1    Chen, B.C.2
  • 11
    • 0037043180 scopus 로고    scopus 로고
    • For a review of proline-catalyzed asymmetric transformations, see: B. List Tetrahedron 58 2002 5573 5590
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 12
    • 0037170944 scopus 로고    scopus 로고
    • For a review of amino acids and peptides as catalysts, see: E.R. Jarvo, and S.J. Miller Tetrahedron 58 2002 2481 2495
    • (2002) Tetrahedron , vol.58 , pp. 2481-2495
    • Jarvo, E.R.1    Miller, S.J.2
  • 14
    • 0035886887 scopus 로고    scopus 로고
    • For a general review on organocatalysis, see: P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 40 2001 3726 3748 and references cited therein
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3726-3748
    • Dalko, P.I.1    Moisan, L.2
  • 15
    • 0034536438 scopus 로고    scopus 로고
    • For a review on Shi ketone-based epoxidation catalyst, see: M. Frohn, and Y. Shi Synthesis 2000 1979 2000 and reference cited therein
    • (2000) Synthesis , pp. 1979-2000
    • Frohn, M.1    Shi, Y.2
  • 38
    • 4444276557 scopus 로고    scopus 로고
    • accepted for publication. doi:10.1016/j.tetlet.2004.08.032
    • This catalyst can catalyze the Mannich-type reactions: Wang, W.; Wang, J.; Li, H. Tetrahedron Lett., accepted for publication. doi:10.1016/j.tetlet. 2004.08.032
    • Tetrahedron Lett.
    • Wang, W.1    Wang, J.2    Li, H.3
  • 39
    • 4444350211 scopus 로고    scopus 로고
    • note
    • We have found this catalyst can efficiently facilitate the asymmetric Aldol and Michael addition reactions
  • 44
    • 4444257143 scopus 로고    scopus 로고
    • WO Patent 9203415, 1992
    • Recently we have developed a more efficient 3-step synthesis of the catalyst from commercially available N-Cbz-l-prolinamide instead of 6-step from N-Cbz-l-Proline reported in the patent: Burch, R. M.; Patch, R. J.; Shearer, B. G.; Perumattam, J. J.; Natalie, K. J., Jr. WO Patent 9203415, 1992
    • Burch, R.M.1    Patch, R.J.2    Shearer, B.G.3    Perumattam, J.J.4    Natalie Jr., K.J.5
  • 45
    • 4444383715 scopus 로고    scopus 로고
    • note
    • 20 mol % I: 15 min, 84% yield, >99% ee; 10 mol % I: 30 min, 80% yield, >99% ee; 5 mol % I: 50 min, 72% yield, >99% ee; 2 mol % I: 2.5 h, 70% yield, >99% ee; 1 mol % I: 6.5 h, 64% yield, >99% ee


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.