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Volumn 9, Issue 11, 2011, Pages 4205-4218

Organic base effects in NHC promoted O- to C-carboxyl transfer; Chemoselectivity profiles, mechanistic studies and domino catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC INDUCTION; CHEMO-SELECTIVITY; DOMINO REACTIONS; IN-SITU; MECHANISTIC STUDIES; MULTISTEP REACTIONS; ORGANIC BASE;

EID: 79956282759     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05160a     Document Type: Article
Times cited : (26)

References (148)
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    • J. L. Moore, T. Rovis, in Topics in Current Chemistry, Vol. 291 (Ed.:, B. List,), Springer, Berlin, 2009, pp. 77-144
    • (2009) Topics in Current Chemistry , vol.291 , pp. 77-144
    • Moore, J.L.1    Rovis, T.2
  • 85
    • 44249108530 scopus 로고    scopus 로고
    • For the recent NHC-catalysed conjugate addition of alkoxides where a Brønsted base catalysed process was proposed see
    • M. A. Schmidt P. Müller M. Movassaghi Tetrahedron Lett. 2008 49 4316 4318
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4316-4318
    • Schmidt, M.A.1    Müller, P.2    Movassaghi, M.3
  • 130
    • 33746584001 scopus 로고    scopus 로고
    • Peris and Vedejs have recently demonstrated a related diastereoselective DMAP-promoted protocol to generate benzofuranone derivatives, although stoichiometric quantities of DMAP (3 eq) are necessary in this transformation as it is employed both as a base and nucleophilic catalyst;
    • C. Burstein S. Tschan X. Xie F. Glorious Synthesis 2006 38 2418 2439
    • (2006) Synthesis , vol.38 , pp. 2418-2439
    • Burstein, C.1    Tschan, S.2    Xie, X.3    Glorious, F.4
  • 132
    • 0034689887 scopus 로고    scopus 로고
    • For other examples of a related procedure involving stoichiometric DMAP catalysis upon a benzofuranone system see
    • E. Vedejs J. Wang Org. Lett. 2000 2 1031 1032
    • (2000) Org. Lett. , vol.2 , pp. 1031-1032
    • Vedejs, E.1    Wang, J.2
  • 137
    • 84981774755 scopus 로고
    • 1H NMR spectroscopic analysis commencing from phenylalanine derived azlactone indicated full conversion to oxazolyl carbonate 4 as the sole reaction product after short reaction times (1 to 15 min), with subsequent slow rearrangement of carbonate 4 to give C-carboxyl-5 observed. This reaction profile is consistent with oxazolyl carbonate 4 being an intermediate in this reaction pathway rather than direct C-carboxylation of the azlactone promoted by the NHC generated from precatalyst 2 under the reaction conditions
    • W. Steglich G. G. Höfle Angew. Chem. Int. Ed. 1968 7 61
    • (1968) Angew. Chem. Int. Ed. , vol.7 , pp. 61
    • Steglich, W.1    Höfle, G.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.