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Volumn 7, Issue 6, 2005, Pages 1101-1103

Increased structural complexity leads to higher activity: Peptides as efficient and versatile catalysts for asymmetric aldol reactions

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBOXYLIC ACID; PEPTIDE; PROLINE;

EID: 18244393987     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0500259     Document Type: Article
Times cited : (260)

References (25)
  • 1
    • 6044269452 scopus 로고    scopus 로고
    • Recent reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175. (b) List, B. Acc. Chem. Res. 2004, 37, 548-557. (c) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5138-5175
    • Dalko, P.I.1    Moisan, L.2
  • 2
    • 4143095871 scopus 로고    scopus 로고
    • Recent reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175. (b) List, B. Acc. Chem. Res. 2004, 37, 548-557. (c) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 548-557
    • List, B.1
  • 3
    • 4143114533 scopus 로고    scopus 로고
    • Recent reviews: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175. (b) List, B. Acc. Chem. Res. 2004, 37, 548-557. (c) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 580-591
    • Notz, W.1    Tanaka, F.2    Barbas III, C.F.3
  • 4
    • 3242806955 scopus 로고    scopus 로고
    • For recent examples, see: (a) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152-2154. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760. (c) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 2152-2154
    • Northrup, A.B.1    Mangion, I.K.2    Hettche, F.3    MacMillan, D.W.C.4
  • 5
    • 1942469514 scopus 로고    scopus 로고
    • For recent examples, see: (a) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152-2154. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760. (c) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5755-5760
    • Tang, Z.1    Jiang, F.2    Cui, X.3    Gong, L.-Z.4    Mi, A.-Q.5    Jiang, Y.-Z.6    Wu, Y.-D.7
  • 6
    • 2942641357 scopus 로고    scopus 로고
    • For recent examples, see: (a) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152-2154. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760. (c) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1983-1986
    • Torii, H.1    Nakadai, M.2    Ishihara, K.3    Saito, S.4    Yamamoto, H.5
  • 7
    • 1842863015 scopus 로고    scopus 로고
    • For recent examples, see: (a) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152-2154. (b) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760. (c) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4790-4791
    • Halland, N.1    Braunton, A.2    Bachmann, S.3    Marigo, M.4    Jørgensen, K.A.5
  • 8
    • 4143141139 scopus 로고    scopus 로고
    • For reviews see: (a) Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610. (b) Berkessel, A. Curr. Opin. Chem. Biol. 2003, 7, 409-419. (c) Jarvo, E. J.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 601-610
    • Miller, S.J.1
  • 9
    • 0037523450 scopus 로고    scopus 로고
    • For reviews see: (a) Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610. (b) Berkessel, A. Curr. Opin. Chem. Biol. 2003, 7, 409-419. (c) Jarvo, E. J.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
    • (2003) Curr. Opin. Chem. Biol. , vol.7 , pp. 409-419
    • Berkessel, A.1
  • 10
    • 0037170944 scopus 로고    scopus 로고
    • For reviews see: (a) Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610. (b) Berkessel, A. Curr. Opin. Chem. Biol. 2003, 7, 409-419. (c) Jarvo, E. J.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
    • (2002) Tetrahedron , vol.58 , pp. 2481-2495
    • Jarvo, E.J.1    Miller, S.J.2
  • 19
    • 18244382907 scopus 로고    scopus 로고
    • note
    • AA1 and AA3 = Gly, D-Val, L-Ala, L-Leu, D-Pro, L-Pro, D-Phe, L-Tyr, D-His, L-His, D-Arg, D-Asp, L-Glu, D-Asn, L-Gln; AA2 = Gly, L-Val, D-Ala, D-Leu, D-Pro, L-Pro, L-Phe, D-Tyr, D-His, L-His, L-Arg, L-Asp, D-Glu, L-Asn, D-Gln.
  • 20
    • 18244403374 scopus 로고    scopus 로고
    • note
    • Control experiments revealed that no red beads were observed when the peptide library was reacted with benzaldehyde 1 in (a) the absence of the ketone or (b) when the peptide library was acetylated.
  • 23
    • 18244404405 scopus 로고    scopus 로고
    • note
    • Under the same reaction conditions, the use of 1 mol % of proline at room temperature did not lead to full conversion even after 4 days. At -20°C, almost no conversion was observed after 4 days with 1 mol % of proline.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.