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Volumn 44, Issue 16, 2005, Pages 2377-2379

Metallophosphite-induced nucleophilic acylation of α,β- unsaturated amides: Facilitated catalysis by a diastereoselective retro [1,4] brook rearrangement

Author keywords

Acylation; Asymmetric catalysis; Rearrangement; Umpolung

Indexed keywords

ACYLATION; CATALYSIS; ORGANOMETALLICS; STEREOCHEMISTRY;

EID: 18044387219     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462795     Document Type: Article
Times cited : (55)

References (35)
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    • for examples of enantioselective intramolecular Stetter reactions, sec: b) D. Enders, K. Breuer, J. Runsink, J. H. Teles, Helv. Chim. Acta 1996, 79, 1899-1902; c) M. S. Kerr, J. Read de Alanix, T. Rovis, J. Am. Chem. Soc. 2002, 124, 10298-10299; d) M. S. Kerr, T. Rovis, J. Am. Chem. Soc. 2004, 126, 8876-8877; e) S. M. Mennen, J. T. Blank, M. B. Tran-Dubé, J. E. Imbriglio, S. J. Miller, Chem. Commun. 2005, 195-197.
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    • 3242812738 scopus 로고    scopus 로고
    • for examples of enantioselective intramolecular Stetter reactions, sec: b) D. Enders, K. Breuer, J. Runsink, J. H. Teles, Helv. Chim. Acta 1996, 79, 1899-1902; c) M. S. Kerr, J. Read de Alanix, T. Rovis, J. Am. Chem. Soc. 2002, 124, 10298-10299; d) M. S. Kerr, T. Rovis, J. Am. Chem. Soc. 2004, 126, 8876-8877; e) S. M. Mennen, J. T. Blank, M. B. Tran-Dubé, J. E. Imbriglio, S. J. Miller, Chem. Commun. 2005, 195-197.
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    • for examples of enantioselective intramolecular Stetter reactions, sec: b) D. Enders, K. Breuer, J. Runsink, J. H. Teles, Helv. Chim. Acta 1996, 79, 1899-1902; c) M. S. Kerr, J. Read de Alanix, T. Rovis, J. Am. Chem. Soc. 2002, 124, 10298-10299; d) M. S. Kerr, T. Rovis, J. Am. Chem. Soc. 2004, 126, 8876-8877; c) S. M. Mennen, J. T. Blank, M. B. Tran-Dubé, J. E. Imbriglio, S. J. Miller, Chem. Commun. 2005, 195-197.
    • (2005) Chem. Commun. , pp. 195-197
    • Mennen, S.M.1    Blank, J.T.2    Tran-Dubé, M.B.3    Imbriglio, J.E.4    Miller, S.J.5
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  • 26
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    • note
    • The racemic TADDOL phosphite 5 regularly provided higher yields than simpler phosphites, for example, diethyl phosphite.
  • 31
    • 18044365334 scopus 로고    scopus 로고
    • CCDC-253985 (4d) and -253984 (8d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
  • 32
    • 18044384553 scopus 로고    scopus 로고
    • note
    • The 2R configuration of 7d was assigned through chemical correlation (sec the Supporting Information).
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    • (Silyloxy)phosphopate anion 2 has been previously prepared stoichiometrically: R. E. Koenigkramer, H. Zimmer, Tetrahedron Lett. 1980, 21, 1017-1020.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.