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Volumn 12, Issue 20, 2006, Pages 5383-5397

Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides

Author keywords

Aldol reaction; Amino acids; Asymmetric catalysis; Ketones; Organocatalysis; Peptides

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC CATALYSIS; ORGANOCATALYSIS; PEPTIDES;

EID: 33745893522     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501639     Document Type: Article
Times cited : (245)

References (126)
  • 1
    • 0003993814 scopus 로고    scopus 로고
    • (Ed.: R. N. Patel), Marcel Dekker, New York
    • a) W.-D Fessner in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker, New York 2000, 239;
    • (2000) Stereoselective Biocatalysis , pp. 239
    • Fessner, W.-D.1
  • 9
    • 0003417469 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming, C.-H. Heathcock), Pergamon, Oxford
    • Comprehensive Organic Synthesis, Vol 2. (Eds.: B. M. Trost, I. Fleming, C.-H. Heathcock), Pergamon, Oxford, 1991.
    • (1991) Comprehensive Organic Synthesis , vol.2
  • 10
    • 33745931513 scopus 로고    scopus 로고
    • For examples of application in total synthesis; see a) T. Mukaiyama, Angew. Chem. 2004, 116, 5708;
    • (2004) Angew. Chem. , vol.116 , pp. 5708
    • Mukaiyama, T.1
  • 14
    • 11844259698 scopus 로고    scopus 로고
    • (Ed.: R. Mahrwald), Wiley-VCH, Weinheim
    • Modern Aldol Reactions, Vols. 1 & 2, (Ed.: R. Mahrwald), Wiley-VCH, Weinheim, 2004;
    • (2004) Modern Aldol Reactions , vol.1-2
  • 15
    • 0003445429 scopus 로고    scopus 로고
    • Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg
    • E. M. Carreira, in Comprehensive Asymmetrie Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999;
    • (1999) Comprehensive Asymmetrie Catalysis
    • Carreira, E.M.1
  • 38
    • 33847804003 scopus 로고
    • For the proline-catalyzed intermolecular aldol reaction; see a) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615;
    • (1974) J. Org. Chem. , vol.39 , pp. 1615
    • Hajos, Z.G.1    Parrish, D.R.2
  • 43
    • 0016842151 scopus 로고
    • For the stoichiometric use of phenylalanine and tyrosine to mediate asymmetric intermolecular aldol condensations; see: d) S. Danishefsky, P. Cain, J. Am. Chem. Soc. 1975, 97, 5282;
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 5282
    • Danishefsky, S.1    Cain, P.2
  • 76
    • 0001551510 scopus 로고    scopus 로고
    • For examples of the use of urea derivatives in catalytic asymmetric synthesis; see: a) M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem. 2000, 2, 1336;
    • (2000) Angew. Chem. , vol.2 , pp. 1336
    • Sigman, M.S.1    Vachal, P.2    Jacobsen, E.N.3
  • 94
    • 33745879303 scopus 로고    scopus 로고
    • note
    • This strategy was first applied to (S)-proline by the groups of Ley, Hayashi, and Arvidsson; see references [11 j-k, m] and references therein.
  • 95
    • 33745899169 scopus 로고    scopus 로고
    • note
    • Similar low enantioselectivity is achieved in the proline-catalyzed aqueous aldol reaction:
  • 108
    • 33745894493 scopus 로고    scopus 로고
    • note
    • Alanine, for example, was oligomerized to di- and trialanine, which catalyzed the asymmetric formation of 2 b with 96% ee under these prebiotic reaction conditions.
  • 110
    • 0030621130 scopus 로고    scopus 로고
    • and are also of extraterrestrial origin; see: J. R. Cronin, S. Pizzarello, Science 1997, 275, 951.
    • (1997) Science , vol.275 , pp. 951
    • Cronin, J.R.1    Pizzarello, S.2
  • 120
    • 0037425534 scopus 로고    scopus 로고
    • L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 2003, 125, 16. For the first observation of a positive nonlinear effect in a proline-catalyzed intermolecular asymmetric aldol reaction; see reference [2c].
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 16
    • Hoang, L.1    Bahmanyar, S.2    Houk, K.N.3    List, B.4
  • 121
    • 33745931517 scopus 로고    scopus 로고
    • note
    • The eutectic is the point at which all three phases - (R)-amino acid, (S)-amino acid, and DMSO - can exist simultaneously. The eutectic point is dependent on the amino acid involved.
  • 122
    • 33745891365 scopus 로고    scopus 로고
    • P. Dziedzic, W. Zou, I. Ibrahem, A. Córdova, unpublished results
    • P. Dziedzic, W. Zou, I. Ibrahem, A. Córdova, unpublished results.
  • 123
    • 23844543306 scopus 로고    scopus 로고
    • For an excellent DFT study of the acyclic amino acid-catalyzed intramolecular aldol reaction; see: F. R. Clemente, K. N. Houk, J. Am. Chem. Soc. 2005, 127, 11294.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11294
    • Clemente, F.R.1    Houk, K.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.