메뉴 건너뛰기




Volumn 64, Issue 14, 1999, Pages 5312-5314

Stereoselective oxidative dimerization of (1R)-camphor. A short synthesis of exo,exo'.3,3'-Biisoborneol

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIKETONE; 3,3' BIISOBORNEOL; CAMPHOR; ENOLATE; SUCCINIC ACID; UNCLASSIFIED DRUG;

EID: 0033043420     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990394g     Document Type: Article
Times cited : (15)

References (28)
  • 16
    • 0008597977 scopus 로고
    • The photolysis of exo- or endo-(1R)-3-bromocamphor proceeds through the enoxy radical 3 in its singlet excited state to give a mixture of 4, 5, and 6 in a ratio of 1:1:2. A solution of KOH in MeOH readily isomerizes 4 to 5 via 6 (Orita, K.; Yorita, K.; Miyazawa, M.; Suginome, H. Synlett 1994, 937-938).
    • (1994) Synlett , pp. 937-938
    • Orita, K.1    Yorita, K.2    Miyazawa, M.3    Suginome, H.4
  • 17
    • 85069278184 scopus 로고    scopus 로고
    • note
    • The configuration of 4 follows from its reduction with LAH (see procedure A, Experimental Section).
  • 18
    • 85069279804 scopus 로고    scopus 로고
    • note
    • 6] was reported to give only the E-isomer 7 (ref 12). For the formation of 7 as a byproduct from bithiocamphor, see ref 13.
  • 21
    • 85069282301 scopus 로고    scopus 로고
    • note
    • It is possible that dimerization of enoxy radicals 3 is indiscriminate (ref 9). The slow release of 3 may favor its stereoelectronically controlled capture by camphor enolate 2 as the rate-determining step (cf. ref 7a).
  • 23
    • 0001316257 scopus 로고
    • Dauben, W. G.; Fonken, G. J.; Noyce, D. S. J. Am. Chem. Soc. 1956, 78, 2579. Brown, H. C.; Deck, H. R. J. Am. Chem. Soc. 1965, 87, 5620.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5620
    • Brown, H.C.1    Deck, H.R.2
  • 24
    • 85069282578 scopus 로고    scopus 로고
    • note
    • The procedure also provides a one-pot synthesis of 4, which previously has only been accomplished by a circuitous route from camphor through the intermediacy of (1R,1R′)-exo,exo′-3,3′-bithiocamphor (refs 12 and 13).
  • 26
    • 0003598098 scopus 로고
    • Scheffold, R., Ed.; Salle and Sauerländer: Aarau
    • Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle and Sauerländer: Aarau, 1983; Vol. 3, p 217. Dahinden, R.; Beck, A. K.; Seebach, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; John Wiley: Chichester, 1995; Vol. 3, p 2167.
    • (1983) Modern Synthetic Methods , vol.3 , pp. 217
    • Seebach, D.1    Weidmann, B.2    Widler, L.3
  • 27
    • 0000057715 scopus 로고
    • Paquette, L., Ed.; John Wiley: Chichester
    • Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle and Sauerländer: Aarau, 1983; Vol. 3, p 217. Dahinden, R.; Beck, A. K.; Seebach, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; John Wiley: Chichester, 1995; Vol. 3, p 2167.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.3 , pp. 2167
    • Dahinden, R.1    Beck, A.K.2    Seebach, D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.