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Volumn 42, Issue 18, 2003, Pages 2060-2063

Highly stereoselective tandem aza-Michael addition-enolate protonation to form partially modified retropeptide mimetics incorporating a trifluoroalanine surrogate

Author keywords

Diastereoselectivity; Michael addition; Peptidomimetics; Protonation; Solvent effects

Indexed keywords

ADDITION REACTIONS; PROTONS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0038587652     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250711     Document Type: Article
Times cited : (82)

References (41)
  • 3
    • 0001215147 scopus 로고
    • b) J. Gante, Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720;
    • (1994) Angew. Chem. , vol.106 , pp. 1780-1802
    • Gante, J.1
  • 4
    • 0028038601 scopus 로고
    • b) J. Gante, Angew. Chem. 1994, 106, 1780-1802; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1699-1720
  • 34
    • 0037894207 scopus 로고    scopus 로고
    • note
    • In toluene the absence of an amine produced a dramatic drop in stereoselectivity (54% de for 4a, Table 1, entry 15). The de also decreased when DABCO was used in a catalytic amount (86% for 4a, Table 1, entry 13).
  • 35
    • 0038231747 scopus 로고    scopus 로고
    • note
    • Faster reactions were also observed when DABCO was used instead of TEA, DIPEA, or TMP.
  • 36
    • 0037556306 scopus 로고    scopus 로고
    • note
    • The crystal structures of 4j and 4n will be published in a full paper.
  • 37
    • 0024430786 scopus 로고
    • The asymmetric addition of chiral alcohols to ketenes ("Merck reaction"), a conceptually related reaction, shows a very similar dependence on the polarity of the solvent and the structure of the catalyst (the amine base). See, for example: a) R. D. Larsen, E. G. Corley, P. Davis, P. J. Reider, E. J. J. Grabowski, J. Am. Chem. Soc. 1989, 111, 7650-7651;
    • (1989) Am. Chem. Soc. , vol.111 , pp. 7650-7651
    • Larsen, R.D.1    Corley, E.G.2    Davis, P.3    Reider, P.J.4    Grabowski, E.J.J.5
  • 41
    • 0034820602 scopus 로고    scopus 로고
    • The tight zwitterionic termolecular (alcohol/ketene/amine) intermediate that was recently proposed to explain the high stereocontrol of the Merck reaction might also be a useful model for a mechanistic interpretation of the reaction presented herein. The latter reaction is probably more complex both from a mechanistic and a stereochemical point of view because of the presence of a double stereoinduction effect: e) C. E. Cannizzaro, T. Strassner, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 2668-2669.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2668-2669
    • Cannizzaro, C.E.1    Strassner, T.2    Houk, K.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.