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Volumn 45, Issue 7, 2006, Pages 1147-1151

Chirally aminated 2-naphthols - organocatalytic synthesis of non-biaryl atropisomers by asymmetric friedel-crafts amination

Author keywords

Amination; Asymmetric synthesis; Friedel Crafts reaction; Naphthols; Organocatalysis

Indexed keywords

AMINATION; COMPUTATIONAL METHODS; FRIEDEL-CRAFTS REACTION; REACTION KINETICS;

EID: 33745438448     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503042     Document Type: Article
Times cited : (231)

References (34)
  • 4
    • 24644462889 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5384-5427.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5384-5427
  • 6
    • 3843110770 scopus 로고    scopus 로고
    • Ed.: J. Clayden
    • Tetrahedron symposium-in-print on atropisomerism (Ed.: J. Clayden), Tetrahedron 2004, 60, 4325-4558;
    • (2004) Tetrahedron , vol.60 , pp. 4325-4558
  • 7
    • 0000021056 scopus 로고    scopus 로고
    • see also: J. Clayden, Angew. Chem. 1997, 109, 986-988;
    • (1997) Angew. Chem. , vol.109 , pp. 986-988
    • Clayden, J.1
  • 10
    • 0002999412 scopus 로고
    • the term atropisomers is generally used for conformers that have a half-life that is arbitrarily defined as longer than 1000 s, see: b) M. Oki, Top. Stereochem. 1983, 14, 1-81.
    • (1983) Top. Stereochem. , vol.14 , pp. 1-81
    • Oki, M.1
  • 24
    • 33746311312 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra (400 MHz) was reported in ref. [8c] without apparently recognizing that 7a is a chiral compound; this splitting is not due to the presence of rotamers.
  • 25
    • 0002773030 scopus 로고
    • A substituent in the 8-position of the binaphthyl moiety does not always correspond to a higher rotational barrier; for example, see: A. S. Cooke, M. M. Harris, J. Chem. Soc. 1963, 2365-2373;
    • (1963) J. Chem. Soc. , pp. 2365-2373
    • Cooke, A.S.1    Harris, M.M.2
  • 28
    • 33746284597 scopus 로고    scopus 로고
    • note
    • 2PHAL (10); PYR = 2,5-diphenyl-4,6-pyrimidinediyl diether, PHAL = 1,4-phthalazinediyl diether.
  • 30
    • 33746284888 scopus 로고    scopus 로고
    • note
    • 1 values afforded lower conversions (15-50% after 4 days) and enantioselectivies (48-69% ee).
  • 31
    • 33746296250 scopus 로고    scopus 로고
    • CCDC-288198 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 34
    • 18844380223 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3086-3089.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3086-3089


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.