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Volumn 9, Issue 2, 2007, Pages 371-374

Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZYL ALCOHOL DERIVATIVE; CARBENE; DRUG DERIVATIVE; ESTER; HETEROCYCLIC COMPOUND; HYDROCARBON; METHANE;

EID: 33846646508     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062940f     Document Type: Article
Times cited : (245)

References (44)
  • 5
    • 28844466070 scopus 로고    scopus 로고
    • For a review of tandem oxidation processes, see
    • For a review of tandem oxidation processes, see: Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851-869.
    • (2005) Acc. Chem. Res , vol.38 , pp. 851-869
    • Taylor, R.J.K.1    Reid, M.2    Foot, J.3    Raw, S.A.4
  • 18
    • 85136551077 scopus 로고    scopus 로고
    • In the absence of manganese(IV) oxide, the combination of aldehydes with triazolium salt E and DBU yielded only benzoin products. See: (a) Breslow, R, Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242
    • In the absence of manganese(IV) oxide, the combination of aldehydes with triazolium salt E and DBU yielded only benzoin products. See: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242.
  • 26
    • 11144327707 scopus 로고    scopus 로고
    • Acyl heteroazolium species have been proposed as acylating agents in several NHC-catalyzed processes. See: (a) Suzuki, Y, Yamauchi, K, Muramatsu, K, Sato, M. Chem. Commun. 2004, 2770-2771
    • Acyl heteroazolium species have been proposed as acylating agents in several NHC-catalyzed processes. See: (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770-2771.
  • 29
    • 33846591463 scopus 로고    scopus 로고
    • In a related, but strongly discouraging result, Taylor reported that 2 full equiv of a thiazolium salt in the presence of 20 equiv of manganese(IV) oxide only afforded 4% yield (calculated by 1H NMR) of methylcinnamate from cinnamyl alcohol see ref 5
    • 1H NMR) of methylcinnamate from cinnamyl alcohol (see ref 5).
  • 31
    • 33846578284 scopus 로고    scopus 로고
    • The use of cis-allylic alcohols in this reaction leads to slower reaction times and partial isomerization of the double bond (1:5 E/Z mixture). n-Butyl cis-cinnamate can be isolated in moderate yield (62%).
    • The use of cis-allylic alcohols in this reaction leads to slower reaction times and partial isomerization of the double bond (1:5 E/Z mixture). n-Butyl cis-cinnamate can be isolated in moderate yield (62%).
  • 35
    • 33846590058 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 40
    • 0001526323 scopus 로고    scopus 로고
    • Resubjecting optically enriched acylated material to reaction conditions led to complete racemization after 90 min. For examples of acyl transfer of monoacylated 1,2-cyclohexane diols, see: Vedejs, E, Daugulis, O, Diver, S. T. J. Org. Chem. 1996, 61, 430-431
    • Resubjecting optically enriched acylated material to reaction conditions led to complete racemization after 90 min. For examples of acyl transfer of monoacylated 1,2-cyclohexane diols, see: Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.