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Volumn 18, Issue 11, 2012, Pages 3362-3370

Stabilization of proline enamine carboxylates by amine bases

Author keywords

aldol reaction; enamines; ion pairs; NMR spectroscopy; organocatalysis

Indexed keywords

ACID FUNCTION; ALDOL REACTIONS; BIFUNCTIONAL ACTIVITY; CONDENSATION PRODUCT; ENAMINE INTERMEDIATES; ENAMINES; IMINIUM; IN-SITU; ION PAIRS; IONIC INTERACTION; ORGANOCATALYSIS; ORGANOCATALYTIC; PROTON RESONANCES; REACTION MECHANISM; STEREOCONTROL;

EID: 84857851932     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102660     Document Type: Article
Times cited : (33)

References (54)
  • 6
  • 37
    • 80054702010 scopus 로고    scopus 로고
    • Blackmond and co-workers could indeed show that the use of tetraalkylammonium prolinates also resulted in a similar reversal of the enantioselectivity as observed for the addition of strong bases. See ref. [10a]. Note added in proof: Enamine carboxylate intermediates were also detected in a very recent study by Armstrong, Blackmond, and Houk
    • Blackmond and co-workers could indeed show that the use of tetraalkylammonium prolinates also resulted in a similar reversal of the enantioselectivity as observed for the addition of strong bases. See ref. [10a]. Note added in proof: Enamine carboxylate intermediates were also detected in a very recent study by Armstrong, Blackmond, and Houk:, J. E. Hein, J. Burés, Y.-h. Lam, M. Hughes, K. N. Houk, A. Armstrong, D. G. Blackmond, Org. Lett. 2011, 13, 5644.
    • (2011) Org. Lett. , vol.13 , pp. 5644
    • Hein, J.E.1    Burés, J.2    Lam, Y.-H.3    Hughes, M.4    Houk, K.N.5    Armstrong, A.6    Blackmond, D.G.7
  • 46
    • 0004087670 scopus 로고
    • (Ed.: Z. Rappoport), Wiley, New York
    • The Chemistry of Enamines, (Ed.:, Z. Rappoport,), Wiley, New York, 1994.
    • (1994) The Chemistry of Enamines
  • 47
    • 0037134880 scopus 로고    scopus 로고
    • It is known that in DMF the formation of aldol condensation products is significantly reduced, see:, A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6798
    • Northrup, A.B.1    MacMillan, D.W.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.