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Volumn 64, Issue 26, 1999, Pages 9430-9443

Configurationally stable biaryl analogues of 4-(dimethylamino)pyridine: A novel class of chiral nucleophilic catalysts

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

EID: 0033601316     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991011h     Document Type: Article
Times cited : (102)

References (89)
  • 9
    • 0002244727 scopus 로고
    • (a) Litvinenko, L. M.; Kirichenko, A. I. Doklady Chem. (Engl. Transl.) 1967, 763-766 [Dokl. Akad. Nauk. SSSR 1967, 176, 97-100].
    • (1967) Dokl. Akad. Nauk. SSSR , vol.176 , pp. 97-100
  • 43
    • 0342658160 scopus 로고    scopus 로고
    • note
    • 3SiH (ref 20), however, allowed for a high yield of the deprotected product to be isolated.
  • 49
    • 0343964198 scopus 로고    scopus 로고
    • note
    • The ability of biaryl 35 to induce α-elimination of HCl from dichloromethane was noted during the growth of a single crystal from an ether/dichloromethane solution. The crystal grown was demonstrated to be hydrochloride of biaryl 35 by single-crystal X-ray analysis.
  • 50
    • 0343964197 scopus 로고    scopus 로고
    • note
    • 1H NMR signals for methylene protons gave a more complex splitting pattern at 243 K (similar to that of biaryl 28). For biaryl 29 no decoalescence was observed even at 223 K.
  • 51
    • 0343092424 scopus 로고    scopus 로고
    • note
    • 3). The effect is more pronounced for naphthyl derivatives 31 and 55 (-0.69 and -0.70 ppm, respectively, relative to 16) than for phenyl analogue 25 (-0.34 ppm).
  • 60
    • 0002999412 scopus 로고
    • Allinger, N. L., Eliel, N. L., Wilen, S. H., Eds.; John Wiley & Sons: New York
    • Ôki, M. In Topics in Stereochemistry; Allinger, N. L., Eliel, N. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1983; Vol. 14, pp 1-81.
    • (1983) Topics in Stereochemistry , vol.14 , pp. 1-81
    • Ôki, M.1
  • 61
    • 0342658155 scopus 로고    scopus 로고
    • Spivey, A. C.; Hochmuth, D.H.; Fekner, T., unpublished results
    • Spivey, A. C.; Hochmuth, D.H.; Fekner, T., unpublished results.
  • 68
    • 0343964193 scopus 로고    scopus 로고
    • note
    • X-ray single-crystal structures of biaryl 38 and its N-oxide are almost superimposable, suggesting a high level of across-ring conjugation in the parent molecule 38.
  • 79
    • 0343964191 scopus 로고    scopus 로고
    • note
    • Prepared by an analogous route to that described for the preparation of biaryl 55 via low-yielding (13%) Suzuki cross-coupling of aryl bromide 36 with arylboronic acid 51. Various attempts to accomplish a similar coupling with aryl bromide 41 failed.
  • 82
    • 0343964189 scopus 로고    scopus 로고
    • note
    • Prepared from 1-bromo-3-methoxynaphthalene (ref 45) according to the procedure described for the preparation of arylboronic acid 51.
  • 88
    • 0343528365 scopus 로고    scopus 로고
    • note
    • 13C NMR, which can be attributed to a small amount of the anhydride formed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.