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Volumn 5, Issue 4, 2007, Pages 606-609

An enantioselective Brønsted acid catalyzed enamine Mannich reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSTS; KETONES; TOLUENE;

EID: 33846952876     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b616143j     Document Type: Article
Times cited : (32)

References (60)
  • 17
    • 30444441133 scopus 로고    scopus 로고
    • and references cited therein Reviews on asymmetric organocatalysis:
    • M. M. B. Marques Angew. Chem., Int. Ed. 2006 45 348 352
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 348-352
    • Marques, M.M.B.1
  • 20
    • 0037043180 scopus 로고    scopus 로고
    • B. List Tetrahedron 2002 58 5573 5590
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 27
    • 33746277515 scopus 로고    scopus 로고
    • For selected examples of enantioselective, cyclic secondary amine catalyzed, Mannich reactions see:
    • S. J. Connon Chem.-Eur. J. 2006 12 5418 5427
    • (2006) Chem.-Eur. J. , vol.12 , pp. 5418-5427
    • Connon, S.J.1
  • 47
    • 0034721440 scopus 로고    scopus 로고
    • In some examples the desired products can still be formed in high enantioselectivities see:
    • B. List J. Am. Chem. Soc. 2000 122 9336 9337
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336-9337
    • List, B.1
  • 56
    • 0037032312 scopus 로고    scopus 로고
    • Enamines substituted on the nucleophilic carbon were substantially less reactive With cyclohexanone derived morpholino enamine under the same reaction conditions the conversion of the catalyzed reaction after 15 hours was disappointingly 18% versus 5% for the uncatalyzed reaction. An ee of 12% was observed for the major diastereomer When N-Boc alkyl imines were employed under the same reaction conditions a significant drop in ee was observed. In the case of the cyclohexanecarboxaldehyde derived imine the desired product was isolated in 60% yield with a 26% ee
    • A. G. Wenzel E. N. Jacobsen J. Am. Chem. Soc. 2002 124 12964 12965
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12964-12965
    • Wenzel, A.G.1    Jacobsen, E.N.2
  • 58
    • 0035807577 scopus 로고    scopus 로고
    • 2) = 0.110 [I > 2σ(I)]. The structure was solved with SHELXS-97, and refined with SHELXL-97. CCDC reference number 626419. For crystallographic data in CIF or other electronic format see DOI:
    • J. Rudolph F. Hannig H. Theis R. Wischnat Org. Lett. 2001 3 3153 3155
    • (2001) Org. Lett. , vol.3 , pp. 3153-3155
    • Rudolph, J.1    Hannig, F.2    Theis, H.3    Wischnat, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.