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Volumn 47, Issue 19, 2008, Pages 3631-3634

The enantioselective, brønsted acid catalyzed, vinylogous Mannich reaction

Author keywords

Asymmetric catalysis; C C coupling; Contact ion pairs; Organocatalysis; Phosphoric acid

Indexed keywords

AMINES; CHEMICAL REACTIONS; ESTERS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PHOSPHORIC ACID; SILANES;

EID: 53249126965     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800103     Document Type: Article
Times cited : (155)

References (66)
  • 9
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    • for a conceptually different approach towards vinylogous Mannich products, see M. Lautens, E. Tayama, D. Nguyen, Org. Lett. 2004, 6, 345.
    • d) for a conceptually different approach towards vinylogous Mannich products, see M. Lautens, E. Tayama, D. Nguyen, Org. Lett. 2004, 6, 345.
  • 24
    • 38349189109 scopus 로고    scopus 로고
    • and references therein
    • c) T. Akiyama, Chem. Rev. 2007, 107, 5744, and references therein.
    • (2007) Chem. Rev , vol.107 , pp. 5744
    • Akiyama, T.1
  • 25
    • 24044465512 scopus 로고    scopus 로고
    • Reduction of imines with Hantzsch esters: see, for example, a M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
    • Reduction of imines with Hantzsch esters: see, for example, a) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
  • 35
    • 53549112334 scopus 로고    scopus 로고
    • Aza Diels-Alder reactions with imines: see, for example, a J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
    • Aza Diels-Alder reactions with imines: see, for example, a) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
  • 39
    • 4644355914 scopus 로고    scopus 로고
    • Friedel-Crafts reactions with imines: see, for example, a D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804;
    • Friedel-Crafts reactions with imines: see, for example, a) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804;
  • 43
    • 33746282355 scopus 로고    scopus 로고
    • For a selection of further applications with imines see: a
    • For a selection of further applications with imines see: a) M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312;
    • (2006) Angew. Chem , vol.118 , pp. 2312
    • Terada, M.1    Machioka, K.2    Sorimachi, K.3
  • 53
    • 33845248151 scopus 로고    scopus 로고
    • For a selection of other applications, see: a
    • For a selection of other applications, see: a) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
    • (2006) Angew. Chem , vol.118 , pp. 4299
    • Mayer, S.1    List, B.2
  • 63
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    • 4 94:6.
    • 4 94:6.
  • 64
    • 53549106493 scopus 로고    scopus 로고
    • Contact ion pair 6a (m/z = 1024) cleanly fragments during collision experiments in the ion trap into product 3a (m/z = 326) and the silyl ester of phosphoric acid 4e (m/z = 699).
    • Contact ion pair 6a (m/z = 1024) cleanly fragments during collision experiments in the ion trap into product 3a (m/z = 326) and the silyl ester of phosphoric acid 4e (m/z = 699).
  • 65
    • 53549131840 scopus 로고    scopus 로고
    • The absolute configuration of the products was assigned by conversion of the related ethyl (2E,5S)-5-phenylamino-5-(4-chlorophenyl)-2- pentenoate (e.r. 92:8) into the saturated acid followed by comparison of the rotation value with reported data (see the Supporting Information).
    • The absolute configuration of the products was assigned by conversion of the related ethyl (2E,5S)-5-phenylamino-5-(4-chlorophenyl)-2- pentenoate (e.r. 92:8) into the saturated acid followed by comparison of the rotation value with reported data (see the Supporting Information).
  • 66
    • 53549088683 scopus 로고    scopus 로고
    • Note added in proof: Akiyama et al. reported on a phosphoric acid catalyzed, vinylogous Mannich reaction of 2-silyloxyfurans: T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399.
    • Note added in proof: Akiyama et al. reported on a phosphoric acid catalyzed, vinylogous Mannich reaction of 2-silyloxyfurans: T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.