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Volumn 50, Issue 10, 2011, Pages 2350-2353

Tosylhydrazide-promoted palladium-catalyzed reaction of β-aminoketones with o-dihaloarenes: Combining organocatalysis and transition-metal catalysis

Author keywords

Arenes; Cascade reactions; Ketones; Palladium; Tandem catalysis

Indexed keywords

ARENES; CASCADE REACTIONS; CHEMICAL EQUATIONS; CROSS-COUPLINGS; INTRAMOLECULAR AMINATION; METAL CATALYSIS; ORGANOCATALYSIS; ORGANOCATALYTIC; PALLADIUM-CATALYZED REACTIONS; PHENANTHRIDINE; QUINOLINE DERIVATIVE; TANDEM CATALYSIS;

EID: 79952053625     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006996     Document Type: Article
Times cited : (75)

References (41)
  • 4
    • 18844396659 scopus 로고    scopus 로고
    • For relevant examples of auto-tandem Pd-catalyzed processes, see
    • For relevant examples of auto-tandem Pd-catalyzed processes, see: a) M. C. Willis, G. N. Brace, I. P. Holmes, Angew. Chem. 2005, 117, 407;
    • (2005) Angew. Chem. , vol.117 , pp. 407
    • Willis, M.C.1    Brace, G.N.2    Holmes, I.P.3
  • 17
    • 77950493901 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2010, 49, 2909, and references therein.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2909
  • 21
    • 79952051812 scopus 로고    scopus 로고
    • note
    • In previous contributions it has been observed that the C-C bond-forming reaction occurs preferentially over a Pd-catalyzed amination with secondary amines (Ref. [5]).
  • 32
    • 78449312221 scopus 로고    scopus 로고
    • We have recently reported that the cross-coupling reaction of tosylhydrazones derived from a-chiral ketones proceeds with preservation of the chirality
    • We have recently reported that the cross-coupling reaction of tosylhydrazones derived from a-chiral ketones proceeds with preservation of the chirality: J. Barluenga, M. Escribano, F. Aznar, C. Valdés, Angew. Chem. 2010, 122, 7008;
    • (2010) Angew. Chem. , vol.122 , pp. 7008
    • Barluenga, J.1    Escribano, M.2    Aznar, F.3    Valdés, C.4
  • 36
    • 79952053917 scopus 로고    scopus 로고
    • note
    • Although the Mannich reaction gives rise to a mixture of two diastereomers, they could be separated at the tosylhydrazone stage, and thus the Pd-catalyzed cascade reaction was carried out with a single diastereoisomer.
  • 40
    • 79952067166 scopus 로고    scopus 로고
    • note
    • In our hands, attempts to isolate the Mannich adducts prior to formation of the hydrazone led to partial epimerization.
  • 41
    • 79952052417 scopus 로고    scopus 로고
    • note
    • The Mannich reaction leads to a mixture of diastereoisomers that could not be separated, and therefore were employed as a mixture in the Pd-catalyzed cascade reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.