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Volumn 63, Issue 48, 2007, Pages 11886-11892

Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide

Author keywords

Aldol reactions; NOBIN; Organocatalysis; Prolinamides

Indexed keywords

ALDEHYDE; AMIDE; DIOXANE; KETONE; ORGANIC COMPOUND; PROLINE DERIVATIVE; SOLVENT; WATER;

EID: 35348850061     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.027     Document Type: Article
Times cited : (70)

References (71)
  • 1
    • 1942512117 scopus 로고
    • Trost B.M., Fleming I., and Heathcock C.H. (Eds), Pergamon, Oxford
    • Kim B.M., Williams S.F., and Masamune S. In: Trost B.M., Fleming I., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 229
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 229
    • Kim, B.M.1    Williams, S.F.2    Masamune, S.3
  • 6
    • 35348897572 scopus 로고    scopus 로고
    • See Ref 9a;
  • 14
    • 35348852912 scopus 로고    scopus 로고
    • See Ref. 9c;
  • 40
    • 35348822802 scopus 로고    scopus 로고
    • See Ref. 12.
  • 48
    • 34248585917 scopus 로고    scopus 로고
    • While this manuscript was in preparation a contribution on the employment of NOBIN-prolinamides in aldol reactions was published:
    • While this manuscript was in preparation a contribution on the employment of NOBIN-prolinamides in aldol reactions was published:. Wang C., Jiang Y., Zhang X.-X., Huang Y., Li B.-G., and Zhang G.-L. Tetrahedron Lett. 48 (2007) 4281
    • (2007) Tetrahedron Lett. , vol.48 , pp. 4281
    • Wang, C.1    Jiang, Y.2    Zhang, X.-X.3    Huang, Y.4    Li, B.-G.5    Zhang, G.-L.6
  • 58
    • 35348817068 scopus 로고    scopus 로고
    • note
    • In solvent screening it was found that higher enantioselectivity but moderate conversions to the aldol product can be achieved in ethereal solvents.
  • 69
    • 28944453814 scopus 로고    scopus 로고
    • α-Chloroacetone displayed a low reactivity in the direct aldol reaction promoted by l-prolinamide derivatives, which had to be used in up to 50 mol % loading to achieve satisfactory yields of the products, see:
    • α-Chloroacetone displayed a low reactivity in the direct aldol reaction promoted by l-prolinamide derivatives, which had to be used in up to 50 mol % loading to achieve satisfactory yields of the products, see:. He L., Tang Z., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Tetrahedron: Asymmetry 62 (2006) 346
    • (2006) Tetrahedron: Asymmetry , vol.62 , pp. 346
    • He, L.1    Tang, Z.2    Cun, L.-F.3    Mi, A.-Q.4    Jiang, Y.-Z.5    Gong, L.-Z.6
  • 70
    • 34250726521 scopus 로고    scopus 로고
    • For an interesting discussion on the role of water in organocatalyzed reactions, see:
    • For an interesting discussion on the role of water in organocatalyzed reactions, see:. Blackmond D.G., Armstrong A., Coombe V., and Wells A. Angew. Chem., Int. Ed. 46 (2007) 3798
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3798
    • Blackmond, D.G.1    Armstrong, A.2    Coombe, V.3    Wells, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.