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Volumn , Issue 11, 2006, Pages 1191-1193

Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; IMINE; MALONIC ACID DERIVATIVE;

EID: 33644747543     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b515725k     Document Type: Article
Times cited : (228)

References (50)
  • 1
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    • B. M. Trost and I. Flemming, Pergamon Press, New York, vol. 2, ch. 4.1
    • E. F. Kleinmann, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Flemming, Pergamon Press, New York, vol. 2, ch. 4.1
    • Comprehensive Organic Synthesis, ed.
    • Kleinmann, E.F.1
  • 24
    • 15244343428 scopus 로고    scopus 로고
    • for the pioneering proline-catalysed asymmetric Mannich reaction see:
    • J. Seayad B. List Org. Biomol. Chem. 3 719 724
    • Org. Biomol. Chem. , vol.3 , pp. 719-724
    • Seayad, J.1    List, B.2
  • 25
    • 0034721440 scopus 로고    scopus 로고
    • Asymmetric organocatalysed Mannich reaction with ketene silyl acetal:
    • B. List J. Am. Chem. Soc. 122 9336 9337
    • J. Am. Chem. Soc. , vol.122 , pp. 9336-9337
    • List, B.1
  • 31
    • 23844490047 scopus 로고    scopus 로고
    • All N-Boc imine substrates were made using the procedure reported by Wenzel and Jacobsen. 6a N-Cbz substrates were synthesized using a method adapted from the Jacobsen procedure (see supporting information)
    • S. Lou B. M. Taoka A. Ting S. E. Schaus J. Am. Chem. Soc. 127 11256 11257
    • J. Am. Chem. Soc. , vol.127 , pp. 11256-11257
    • Lou, S.1    Taoka, B.M.2    Ting, A.3    Schaus, S.E.4
  • 46
    • 28544451072 scopus 로고    scopus 로고
    • It has recently been reported that the unnatural 9-epi-Cinchona derived catalysts are more active than those based on the natural Cinchona skeleton, see ref. 11b Major enantiomer was (S). Confirmed by comparison of HPLC traces for the same compound found in ref. 8
    • A. Lattanzi Org. Lett. 7 2579 2582
    • Org. Lett. , vol.7 , pp. 2579-2582
    • Lattanzi, A.1
  • 47
    • 33644760833 scopus 로고    scopus 로고
    • Enantiomeric excess was not determined accurately, as complete separation of enantiomers was not possible. HPLC traces using a Daicel CHIRALCEL OJ, 25 cm × 0.46 cm column indicated an ee ca. 50%
    • Enantiomeric excess was not determined accurately, as complete separation of enantiomers was not possible. HPLC traces using a Daicel CHIRALCEL OJ, 25 cm × 0.46 cm column indicated an ee ca. 50%
  • 48
    • 33644787416 scopus 로고    scopus 로고
    • 3)
    • These initial results were first disclosed on 20th July 2005 at the 19th International Symposium: Synthesis in Organic Chemistry, University of Oxford


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.