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Volumn 125, Issue 18, 2003, Pages 5262-5263

Novel small organic molecules for a highly enantioselective direct aldol reaction

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZALDEHYDE; ACETONE; ALDEHYDE DERIVATIVE; ALPHA,BETA HYDROXYAMINE; AMINE; BENZALDEHYDE; HYDROXYL GROUP; PROLINE; PYRROLIDINE 2 CARBOXAMIDE; PYRROLIDINE 2 CARBOXYLIC ACID (2' HYDROXYL 1',2' DIPHENYLETHYL)AMINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037955602     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034528q     Document Type: Article
Times cited : (483)

References (44)
  • 1
    • 0000699983 scopus 로고    scopus 로고
    • Mukaiyama aldol reaction
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Chapter 291
    • (a) Carreira, E. M.; Mukaiyama Aldol Reaction. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 29.1.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Carreira, E.M.1
  • 6
    • 0026418434 scopus 로고
    • (a) Trost, B. M. Science 1991. 254. 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 29
  • 30
  • 32
    • 0037582543 scopus 로고    scopus 로고
    • note
    • A poor yield of 6% with 70% ee for 4a and a trace amount of 4j were observed with aldol reactions catalyzed by 20 mol % L-proline under the described reaction conditions (acetone, -25 °C) for 48 h.
  • 34
    • 0038258040 scopus 로고    scopus 로고
    • note
    • All calculations were performed with the Gaussian 98 program.
  • 40
    • 0037151592 scopus 로고    scopus 로고
    • For studies on hydrogen bonds acting like Lewis acid, see: (a) Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 9662. (b) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217. (c) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9662
    • Huang, Y.1    Rawal, V.H.2
  • 41
    • 0037165402 scopus 로고    scopus 로고
    • For studies on hydrogen bonds acting like Lewis acid, see: (a) Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 9662. (b) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217. (c) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
    • (2002) Org. Lett. , vol.4 , pp. 217
    • Schreiner, P.R.1    Wittkopp, A.2
  • 42
    • 0037189898 scopus 로고    scopus 로고
    • For studies on hydrogen bonds acting like Lewis acid, see: (a) Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 9662. (b) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217. (c) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10012
    • Vachal, P.1    Jacobsen, E.N.2
  • 43
    • 0038596707 scopus 로고    scopus 로고
    • note
    • 2O = 1:1) at room temperature, which demonstrates that the hydrogen bond exists in the transition state (see ref 6b).
  • 44
    • 0037582540 scopus 로고    scopus 로고
    • note
    • Dipeptide Pro-Thr-Me catalyzes the direct asymmetric aldol reaction of 4-nitrobenzaldehyde with acetone in 69% ee at room temperature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.