메뉴 건너뛰기




Volumn 12, Issue 16, 2006, Pages 4362-4371

Synthesis of small tripeptide molecules through a catalysis sequence comprising metathesis and aminohydroxylation

Author keywords

Amino acids; Amino hydroxylation; Homogeneous catalysis; Metathesis; Organocatalysis; Peptides

Indexed keywords

AMINO ACIDS; CATALYSIS; ESTERS; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33744794864     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501123     Document Type: Article
Times cited : (16)

References (56)
  • 5
    • 3843107553 scopus 로고    scopus 로고
    • For an excellent review on diversity-oriented synthesis, see: M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48;
    • (2004) Angew. Chem. , vol.116 , pp. 48
    • Burke, M.D.1    Schreiber, S.L.2
  • 10
    • 0004249010 scopus 로고
    • (Eds.: M. Bodanszky, A. Bodanszky), Springer, Berlin
    • d) Principles of Peptide Synthesis (Eds.: M. Bodanszky, A. Bodanszky), Springer, Berlin, 1984.
    • (1984) Principles of Peptide Synthesis
  • 13
    • 24044507147 scopus 로고    scopus 로고
    • For an excellent review on the extension of proteins through nonnatural amino acids, see: L. Wang, P.C. Schultz, Angew. Chem. 2005, 117, 34;
    • (2005) Angew. Chem. , vol.117 , pp. 34
    • Wang, L.1    Schultz, P.C.2
  • 19
    • 33744790403 scopus 로고    scopus 로고
    • http://nobelprize.org/chemistry/laureates/2005/
  • 31
    • 27844553840 scopus 로고    scopus 로고
    • Longer reaction times appear to result in higher yields for compounds 1d and 1e, but the reaction for β-amino acids has still to be optimized. Structurally related acrylamides were found to reach complete conversion at longer reaction times: J. Streuff, K. Muñiz, J. Organomet. Chem. 2005, 690, 5973.
    • (2005) J. Organomet. Chem. , vol.690 , pp. 5973
    • Streuff, J.1    Muñiz, K.2
  • 32
    • 3943048796 scopus 로고    scopus 로고
    • For related tandem catalysis processes that are initiated by ruthenium metathesis, see: a) B. Schmidt. Eur. J. Org. Chem. 2004, 1865;
    • (2004) Eur. J. Org. Chem. , pp. 1865
    • Schmidt, B.1
  • 44
    • 0037784368 scopus 로고    scopus 로고
    • There is literature precedence for the intentional use of N-tosylated α,β-hydroxy amino acids as ligands in second-cycle aminohydroxylation; M. A. Andersson, R. Epple, V. V. Fokin, K.B. Sharpless, Angew. Chem. 2002, 114, 490;
    • (2002) Angew. Chem. , vol.114 , pp. 490
    • Andersson, M.A.1    Epple, R.2    Fokin, V.V.3    Sharpless, K.B.4
  • 45
    • 0036462501 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 472. The observed ee values from these reactions are below 60% and match the de values from our reactions presented here.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 472
  • 46
    • 33744831587 scopus 로고    scopus 로고
    • Diploma Thesis, Universität Bonn (Germany)
    • Related investigations on the stereochemical course within the aminohydroxylation of chiral non-racemic acrylamides revealed that complete regio- and stereoselectivity is possible for this class of substrate: a) J. Streuff, Diploma Thesis, Universität Bonn (Germany). 2005;
    • (2005)
    • Streuff, J.1
  • 51
    • 0003330307 scopus 로고    scopus 로고
    • For examples on asymmetric catalysis employing chiral catalysts in diversified organic synthesis, see ref. [3] and: R. A. Stavanger, S. L. Schreiber, Angew. Chem. 2001, 113, 3525;
    • (2001) Angew. Chem. , vol.113 , pp. 3525
    • Stavanger, R.A.1    Schreiber, S.L.2
  • 53
    • 33744780272 scopus 로고    scopus 로고
    • See Experimental Section for details
    • See Experimental Section for details.
  • 55
    • 0036357988 scopus 로고    scopus 로고
    • b) M. Hamada, A. Dobashi, Anal. Sci. 2002, 18, 83. The literature data in the latter article appears to contain an incorrect NMR interpretation. The correct data set is given in the Experimental Section.
    • (2002) Anal. Sci. , vol.18 , pp. 83
    • Hamada, M.1    Dobashi, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.