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Volumn 127, Issue 50, 2005, Pages 17622-17623

Catalytic enantioselective aza-Henry reaction with broad substrate scope

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE DERIVATIVE; HETEROCYCLIC COMPOUND; SULFONE; UNCLASSIFIED DRUG;

EID: 29344438414     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056594t     Document Type: Article
Times cited : (195)

References (50)
  • 4
  • 16
    • 29344448067 scopus 로고    scopus 로고
    • For one exception using preformed silylnitronates, see ref 5f
    • For one exception using preformed silylnitronates, see ref 5f.
  • 19
    • 29344447123 scopus 로고    scopus 로고
    • Chiral α-amido sulfones as azomethine precursors in aza-Henry processes: (a) Ballini, R.; Petrini, M. Tetrahedron Lett. 1999, 64, 8970-8972.
    • (1999) Tetrahedron Lett , vol.64 , pp. 8970-8972
    • Ballini, R.1    Petrini, M.2
  • 22
    • 29344444373 scopus 로고    scopus 로고
    • ref 6a,c
    • Aromatic N-acyl imines can be obtained as isolable, relatively stable compounds upon treatment with stoichiometric potassium carbonate. See: (a) ref 6a,c.
  • 26
    • 0042880949 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028.
    • (2003) Chem. Rev. , vol.103 , pp. 3013-3028
    • Maruoka, K.1    Ooi, T.2
  • 32
    • 29344471518 scopus 로고    scopus 로고
    • note
    • For 3a: 48% ee in toluene (90% conv.); 18% ee in trifluoromethylbenzene (60% conv.). The selectivity could be improved up to 70% ee in a 1:1 mixture of toluene and dichloromethane.
  • 36
    • 29344445721 scopus 로고    scopus 로고
    • ref 12
    • O-alkylation of cinchone derivatives has proven to provide more efficient catalysts for PTC: (a) ref 12.
  • 37
    • 29344450478 scopus 로고    scopus 로고
    • ref 13
    • (b) ref 13.
  • 45
    • 29344434124 scopus 로고    scopus 로고
    • note
    • For assignment of the configuration of adducts 3 and 11, see the Supporting Information.
  • 46
    • 0033607471 scopus 로고    scopus 로고
    • Mannich reaction
    • For representative transformations eventually amenable for PTC, see the following. Alkinyl-metal additions: (a) Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970-8972. Mannich reaction:
    • (1999) J. Org. Chem. , vol.64 , pp. 8970-8972
    • Mecozzi, T.1    Petrini, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.