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Volumn 10, Issue 10, 2008, Pages 2039-2041

Facile synthesis of c/s-2-alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE; SILANE DERIVATIVE;

EID: 47049085582     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800423m     Document Type: Article
Times cited : (13)

References (33)
  • 22
    • 34948832038 scopus 로고    scopus 로고
    • For an excellent review of semi-pinacol rearrangements, see
    • For an excellent review of semi-pinacol rearrangements, see: Snape, T. J. Chem. Sot: Rev. 2007, 36, 1823.
    • (2007) Chem. Sot: Rev , vol.36 , pp. 1823
    • Snape, T.J.1
  • 27
    • 58149181923 scopus 로고    scopus 로고
    • The alcohol 7b was too hindered to allow formation of the TBS ether, so the TES ether 7a was used instead.
    • The alcohol 7b was too hindered to allow formation of the TBS ether, so the TES ether 7a was used instead.
  • 28
    • 58149185666 scopus 로고    scopus 로고
    • This byproduct 9 is seen whenever there is a methyl substituent α to the epoxide and the rearrangement is relatively slow.3f
    • 3f
  • 29
    • 0003050412 scopus 로고    scopus 로고
    • trans-3-Hydroxy 2-methylcyclohexanone: Corey, E. J.: Melvin, L. S., Jr.; Haslanger, M. F. Tetrahedron Lett. 1975, 16, 3117.
    • (a) trans-3-Hydroxy 2-methylcyclohexanone: Corey, E. J.: Melvin, L. S., Jr.; Haslanger, M. F. Tetrahedron Lett. 1975, 16, 3117.
  • 30
    • 0000484771 scopus 로고    scopus 로고
    • trans-3-Hydroxy- and 3-silyloxy-2-butylcyclohexanone: Tanner, D.; Sellen. M.; Baeckvall, J. E. J. Org. Chem. 1989, 54, 3374.
    • (b) trans-3-Hydroxy- and 3-silyloxy-2-butylcyclohexanone: Tanner, D.; Sellen. M.; Baeckvall, J. E. J. Org. Chem. 1989, 54, 3374.
  • 31
    • 10244240642 scopus 로고    scopus 로고
    • cis-3-Silyloxy-2,6,6-trimethylcyclohexanone: Keränen, M. D.; Kot, K.; Hollmann, C; Eilbracht P. Org. Biomol. Chem. 2004, 2, 3379.
    • (c) cis-3-Silyloxy-2,6,6-trimethylcyclohexanone: Keränen, M. D.; Kot, K.; Hollmann, C; Eilbracht P. Org. Biomol. Chem. 2004, 2, 3379.
  • 32
    • 58149200116 scopus 로고    scopus 로고
    • The stereochemistry of these compounds were assigned by analogy to the earlier analogues 8 and 11.
    • The stereochemistry of these compounds were assigned by analogy to the earlier analogues 8 and 11.
  • 33
    • 58149189011 scopus 로고    scopus 로고
    • There was a strong NOE between the proton α to the OTES group and the aldehyde in 17 which was absent from 16.
    • There was a strong NOE between the proton α to the OTES group and the aldehyde in 17 which was absent from 16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.