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Volumn 127, Issue 11, 2005, Pages 3676-3677

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE;

EID: 15744365005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042216x     Document Type: Article
Times cited : (129)

References (18)
  • 2
    • 3843110770 scopus 로고    scopus 로고
    • (b) Tetrahedron Symposium-in-print on Axially Chiral Amides; Clayden, J., Ed.; Tetrahedron 2004, 60, 4325-4558.
    • (2004) Tetrahedron , vol.60 , pp. 4325-4558
    • Clayden, J.1
  • 7
    • 0001163250 scopus 로고    scopus 로고
    • Asymmetric syntheses of atropisomeric anilides through enantiotopic selective deprotonation with a stoichiometric chiral base have been reported by two groups. However, Uemura's method (ref 3a) cannot be applied to the synthesis of ortho-mono-tert-butylanilide, which can effectively work as a chiral molecule. On the other hand, in Simpkins' method (ref 3b), improvement of the chemical yield (40-56%) and application to other substrates except for N-ortho-tert-butylphenyl maleimide are problems for future study, (a) Hata, T.; Koide, H.; Taniguchi, N.; Uemura, M. Org. Lett. 2000, 2, 1907.
    • (2000) Org. Lett. , vol.2 , pp. 1907
    • Hata, T.1    Koide, H.2    Taniguchi, N.3    Uemura, M.4
  • 11
    • 0001054296 scopus 로고    scopus 로고
    • Kinetic resolution of racemic dibromoparacyclophane through PHANEPHOS-Pd-calalyzed amination has been reported (only one example), while to the best of our knowledge, there has been no paper in relalion 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
  • 17
    • 15744389072 scopus 로고    scopus 로고
    • note
    • Resulis with other chiral phosphine ligands (see Supporting Information): Trost ligand (0%), CHIRAPHOS (0%), PHANEPHOS (0%), BPPFOAc (0%), DIOP (20%, 9% ee), Me-DuPhos (16%, 15% ee), Et-FerroTANE (12%, 33% ee), MOP (18%, 52% ee), tol-BINAP (48%, 53% ee), xyl-BINAP (56%, 78% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.