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Volumn 350, Issue 1, 2008, Pages 95-106

A ring-closing metathesis approach to cyclic α,β-dehydroamino acids

Author keywords

1,4 benzoquinone; Enamides; Isomerization; Nitrogen heterocycles; Olefin metathesis

Indexed keywords


EID: 38349183032     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700308     Document Type: Article
Times cited : (24)

References (51)
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    • b) K. Nakamura, T. Isaka, A. Toshima, M. Kodaka, Tetrahedron Lett. 2004, 45, 7221 and references cited therein;
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    • and references cited therein
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    • Zhou, H.1    van der Donk, W.A.2
  • 4
    • 30944437590 scopus 로고    scopus 로고
    • For reviews on the syntheses and reactions of dehydroamino acids, see: a
    • For reviews on the syntheses and reactions of dehydroamino acids, see: a) C. Bonauer, T. Walenzyk, B. König, Synthesis 2006, 1;
    • (2006) Synthesis , pp. 1
    • Bonauer, C.1    Walenzyk, T.2    König, B.3
  • 10
    • 1542332386 scopus 로고    scopus 로고
    • During the course of our investigations, two isolated examples of RCM of dehydroamino acid fragments were reported: a L. Manzoni, M. Colombo, C. Scolastico, Tetrahedron Lett. 2004, 45, 2623;
    • During the course of our investigations, two isolated examples of RCM of dehydroamino acid fragments were reported: a) L. Manzoni, M. Colombo, C. Scolastico, Tetrahedron Lett. 2004, 45, 2623;
  • 29
    • 3943048796 scopus 로고    scopus 로고
    • B. Schmidt, Eur. J. Org. Chem. 2004, 1865, and references cited therein;
    • a) B. Schmidt, Eur. J. Org. Chem. 2004, 1865, and references cited therein;
  • 35
    • 2942678732 scopus 로고    scopus 로고
    • The presence of a ruthenium hydride species has been suggested as a cause for olefin isomerization during RCM in a number of cases: a S. H. Hong, M. H. Day, R. H. Grubbs, J. Am. Chem. Soc. 2004, 126, 7414;
    • The presence of a ruthenium hydride species has been suggested as a cause for olefin isomerization during RCM in a number of cases: a) S. H. Hong, M. H. Day, R. H. Grubbs, J. Am. Chem. Soc. 2004, 126, 7414;
  • 38
    • 34248371021 scopus 로고    scopus 로고
    • For a recent screening to prevent isomerization in cross-metathesis, see
    • For a recent screening to prevent isomerization in cross-metathesis, see: J. Moise, S. Arseniyadis, J. Cossy, Org. Lett. 2007, 9, 1695.
    • (2007) Org. Lett , vol.9 , pp. 1695
    • Moise, J.1    Arseniyadis, S.2    Cossy, J.3
  • 39
    • 0035098712 scopus 로고    scopus 로고
    • THF may coordinate to the metal center, thereby slowing down the catalysis as well as catalyst decomposition: C. W. Bielawski, O. A. Scherman, R. H. Grubbs, Polymer 2001, 42, 4939;
    • a) THF may coordinate to the metal center, thereby slowing down the catalysis as well as catalyst decomposition: C. W. Bielawski, O. A. Scherman, R. H. Grubbs, Polymer 2001, 42, 4939;
  • 40
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    • 3 is capable of halogen-hydride exchange: T. R. Belderrain, R. H. Grubbs, Organometallics 1997, 16, 4001.
    • 3 is capable of halogen-hydride exchange: T. R. Belderrain, R. H. Grubbs, Organometallics 1997, 16, 4001.
  • 43
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    • 4 can coordinate to heteroatoms in substrates, preventing them from interfering with olefin metathesis and enhancing the rate and yield of cyclization: A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130.
    • 4 can coordinate to heteroatoms in substrates, preventing them from interfering with olefin metathesis and enhancing the rate and yield of cyclization: A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.