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Volumn 40, Issue 40, 1999, Pages 7243-7246

Metalloporphyrin-catalyzed regioselective rearrangement of monoalkyl-substituted epoxides into aldehydes

Author keywords

Aldehyde; Iron(III) tetraphenylporphyrin triflate; Monoalkyl substituted epoxide; Rearrangement

Indexed keywords

ALDEHYDE; EPOXIDE; FERRIC ION; METALLOPORPHYRIN;

EID: 0033214357     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01363-5     Document Type: Article
Times cited : (68)

References (23)
  • 1
    • 0001312924 scopus 로고
    • Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: Oxford
    • Reviews: (a) Rickbom, B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: Oxford, 1991; Vol. 3, p. 733.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733
    • Rickbom, B.1
  • 11
    • 0000756755 scopus 로고
    • Several transition metal-mediated transformations of monoalkyl-substituted epoxides into the corresponding methylketones have been reported: (a) Kulasegaram, V.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195.
    • (1994) J. Org. Chem. , vol.59 , pp. 7195
    • Kulasegaram, V.1    Kulawiec, R.J.2
  • 14
    • 37049067518 scopus 로고
    • Yamamoto and co-workers have recently demonstrated that a strong basic reagent, lithium 2,2,6,6-tetramethylpiperidide (LiTMP), can promote the regioselective transformation of monoalkylsubstituted epoxides into aldehydes. This reaction, however, requires more than a stoichiometric amount of LiTMP: Yanagisawa, A.; Yasue, K.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1994, 2103.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 2103
    • Yanagisawa, A.1    Yasue, K.2    Yamamoto, H.3
  • 20
    • 0000169782 scopus 로고
    • 2), and stored over silica gel under reduced pressure (1 mmHg) at 60°C and 110°C, respectively. The identification of these complexes was done by comparison of their UV-vis spectra and cyclic voltammograms with those of authentic compounds: (a) Kastner, M. E.; Scheidt, W. R.; Mashiko, T.; Reed, C. A. J. Am. Chem. Soc. 1978, 100, 666.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 666
    • Kastner, M.E.1    Scheidt, W.R.2    Mashiko, T.3    Reed, C.A.4
  • 23
    • 0009729635 scopus 로고    scopus 로고
    • note
    • 3) δ: 202.6, 43.8, 28.9, 21.8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.