메뉴 건너뛰기




Volumn 128, Issue 39, 2006, Pages 12923-12931

Highly enantioselective synthesis of atropisomeric anilide derivatives through catalytic asymmetric N-arylation: Conformational analysis and application to asymmetric enolate chemistry

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINATION; ATROPISOMERIC ANILIDE; ENANTIOSELECTIVE SYNTHESIS; ENOLATE CHEMISTRY;

EID: 33749514964     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064026n     Document Type: Article
Times cited : (148)

References (85)
  • 1
    • 0000418012 scopus 로고
    • Examples of atropisomeric compounds having an N-C chiral axis: (a) Bock, L. H.; Adams, R. J. Am. Chem. Soc. 1931, 53, 374.
    • (1931) J. Am. Chem. Soc. , vol.53 , pp. 374
    • Bock, L.H.1    Adams, R.2
  • 8
    • 3843110770 scopus 로고    scopus 로고
    • Tetrahedron symposium-in-print on axially chiral amides
    • Clayden, J., Ed.
    • (b) Clayden, J., Ed. Tetrahedron Symposium-in-print on Axially Chiral Amides. Tetrahedron 2004, 60, 4325-4558.
    • (2004) Tetrahedron , vol.60 , pp. 4325-4558
  • 14
    • 33749519514 scopus 로고    scopus 로고
    • note
    • Our papers in relation to optically active atropisomeric anilides:
  • 18
    • 0034686256 scopus 로고    scopus 로고
    • correction
    • (correction: Tetrahedron Lett. 2000, 41, 4997).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4997
  • 22
    • 33749522301 scopus 로고    scopus 로고
    • note
    • Papers in relation to optically active atropisomeric anilides
  • 36
    • 33749533535 scopus 로고    scopus 로고
    • note
    • N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the stereoselective synthesis of optically active forms of these compounds has been reported by several groups.
  • 47
    • 0002795445 scopus 로고
    • Ojima, I., Ed.; VCH Publishers: New York
    • (a) Hayashi, T. In Catalytic Asymmetric Synthesis: Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365.
    • (1994) Catalytic Asymmetric Synthesis , pp. 325-365
    • Hayashi, T.1
  • 58
    • 0001054296 scopus 로고    scopus 로고
    • Kinetic resolution of racemic dibromoparacyclophane through PHANE-PHOS-Pd catalyzed amination has been reported (only one example), while to the best of our knowledge, there has been no paper in relation to catalytic asymmetric aromatic amination with achiral substrates. Rossen, K.; Pye, P. J.; Maliakal, A.; Volante, R. P. J. Org. Chem. 1997, 62, 6462.
    • (1997) J. Org. Chem. , vol.62 , pp. 6462
    • Rossen, K.1    Pye, P.J.2    Maliakal, A.3    Volante, R.P.4
  • 59
    • 33749510412 scopus 로고    scopus 로고
    • note
    • As far as we know, Pd-catalyzed N-arylation with ortho-alkylated anilide derivatives has not been reported.
  • 65
    • 33749531661 scopus 로고    scopus 로고
    • note
    • -1 (85.1 °C). These data were subjected to an Eyring plot to determine the rotational barrier of the racemization.
  • 66
    • 33749512894 scopus 로고    scopus 로고
    • note
    • See Supporting Information in preliminary Communication (ref 12).
  • 68
    • 33749537182 scopus 로고    scopus 로고
    • note
    • Among the N-nitrophenylated products 2a-r, only the NMR spectrum of benzanilide 2m showed a broadening of the signals which may be due to the equilibrium between the E- and Z-rotames.
  • 69
    • 33749511710 scopus 로고    scopus 로고
    • note
    • 1H NMR chart of 2a, 6a-8a at room temperature and 223 K (-50 °C) are shown in Supporting Information.
  • 74
    • 33749536155 scopus 로고    scopus 로고
    • note
    • NOESY experiment of 6a was not investigated because of an overlap of the ortho-hydrogen (Hc) in the N-phenyl group with an other aromatic hydrogen.
  • 83
    • 33749536493 scopus 로고    scopus 로고
    • note
    • In a previous paper (ref 5f). we reported that the larger bond angle [C(O)-N-C] of a six-membered lactam than that of a five-membered lactam resulted in a higher rotational barrier around the N-Ar bond.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.