메뉴 건너뛰기




Volumn 4, Issue 1, 2002, Pages 79-82

Construction of substituted cyclohexanones by reductive cyclization of 7-oxo-2,8-alkadienyl esters

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0012197937     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0169325     Document Type: Article
Times cited : (29)

References (56)
  • 24
    • 0043097578 scopus 로고    scopus 로고
    • Abstracts of Papers, Orlando, FL.; American Chemical Society: Washington, DC : ORGN 010
    • A small portion of these studies were disclosed in a 1996 presentation; see: Kamenecka, T. M.; Ly, S. K.; Overman, L. E. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL.; American Chemical Society: Washington, DC, 1996: ORGN 010.
    • (1996) 212th National Meeting of the American Chemical Society
    • Kamenecka, T.M.1    Ly, S.K.2    Overman, L.E.3
  • 25
    • 0000975755 scopus 로고    scopus 로고
    • For other sequential reactions that are initiated by conjugate reduction with Stryker's reagent, see: (a) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901-1903.
    • (2001) Org. Lett. , vol.3 , pp. 1901-1903
    • Chiu, P.1    Szeto, C.-P.2    Geng, Z.3    Cheng, K.-F.4
  • 29
    • 0042596719 scopus 로고    scopus 로고
    • ref 5a
    • (e) ref 5a.
  • 36
    • 0042596720 scopus 로고    scopus 로고
    • note
    • 3P can be removed from 5 by slurrying the reagent with hexane or benzene under an argon or nitrogen atmosphere and filtering and drying residual 5 under vacuum.
  • 37
    • 0042095713 scopus 로고    scopus 로고
    • note
    • The high stereoselectivity seen in toluene in reductive silylation of 8a with Stryker's reagent suggests the use of this reagent and solvent for stereocontrolled synthesis of other acyclic (Z)-enoxysilanes.
  • 38
    • 0013487871 scopus 로고
    • Diagnostic chemical shifts of the C8 vinylic hydrogens of (Z)- and (E)-15 readily defined their configurations; see: Saunders, W. H.; Xie, L. F. J. Am. Chem. Soc. 1991, 113, 3123-3130.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 3123-3130
    • Saunders, W.H.1    Xie, L.F.2
  • 39
    • 0043097574 scopus 로고    scopus 로고
    • note
    • 16
  • 40
    • 0042095712 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of California, Irvine, CA
    • Ly, S. K. Ph.D. Dissertation, University of California, Irvine, CA, 1998.
    • (1998)
    • Ly, S.K.1
  • 41
    • 0042095705 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of California, Irvine, CA
    • Kamenecka, T. M. Ph.D. Dissertation, University of California, Irvine, CA, 1996.
    • (1996)
    • Kamenecka, T.M.1
  • 42
    • 0008006132 scopus 로고
    • Available in one step and high yield from dimethyl glutarate; see: Wenkert, E.; Schorp, M. K. J. Org. Chem. 1994, 59, 1943-1944.
    • (1994) J. Org. Chem. , vol.59 , pp. 1943-1944
    • Wenkert, E.1    Schorp, M.K.2
  • 46
    • 0041594746 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of crude reaction products.
  • 47
    • 0042596718 scopus 로고    scopus 로고
    • note
    • That epimerization of the carboxyl substituent did not occur under the basic hydrolysis conditions was confirmed by reaction of acid 36 with diazomethane to return 32.
  • 48
    • 0041594738 scopus 로고    scopus 로고
    • note
    • 3P, cyclization of 8b by the conditions reported in Scheme 3 gave 13b and 14b in a 1:1 ratio.
  • 49
    • 0042596717 scopus 로고    scopus 로고
    • note
    • 26 As a result of destabilizing steric interactions between C5 and a Z ester group, (Z)-enoate 9 should also have a reduced propensity to cyclize in the fashion depicted in Figure 1.
  • 50
    • 33751157924 scopus 로고
    • and related references therein
    • Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688-689 and related references therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 688-689
    • Eliel, E.L.1    Satici, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.