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Volumn 17, Issue 20, 2011, Pages 5613-5627

Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[al] process): A simple access to γ-lactols and 4-methylene-γ-lactols

Author keywords

aluminum acetals; bond forming reactions; cyclization; lactols; radical reactions

Indexed keywords

ALUMINUM; HYDROCARBONS; REACTION KINETICS;

EID: 79955578475     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100049     Document Type: Article
Times cited : (14)

References (65)
  • 2
    • 0001216647 scopus 로고
    • in (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, p. , 779
    • D. P. Curran, in Comprehensive Organic Synthesis, Vol. 4 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, p. 715, 779
    • (1991) Comprehensive Organic Synthesis, Vol. 4 , pp. 715
    • Curran, D.P.1
  • 5
    • 0004269715 scopus 로고    scopus 로고
    • (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim
    • Radicals in Organic Synthesis (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, 2001
    • (2001) Radicals in Organic Synthesis
  • 7
    • 79955574055 scopus 로고    scopus 로고
    • Successful cyclizations of α-halo esters have been reported in refluxing benzene or toluene when using slow addition techniques
    • Successful cyclizations of α-halo esters have been reported in refluxing benzene or toluene when using slow addition techniques
  • 18
    • 33645559650 scopus 로고
    • Another practical solution to achieve efficient cyclization of α-halo esters based on the halogen atom transfer method has been reported.
    • Another practical solution to achieve efficient cyclization of α-halo esters based on the halogen atom transfer method has been reported:, D. P. Curran, C.-T. Chang, J. Org. Chem. 1989, 54, 3140-3157.
    • (1989) J. Org. Chem. , vol.54 , pp. 3140-3157
    • Curran, D.P.1    Chang, C.-T.2
  • 19
    • 79955607895 scopus 로고    scopus 로고
    • For selected examples of oxidation of the cyclic acetal in the presence of acid-sensitive functionalities, see
    • For selected examples of oxidation of the cyclic acetal in the presence of acid-sensitive functionalities, see
  • 26
    • 73249153367 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9549-9552.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9549-9552
  • 41
    • 79955587497 scopus 로고    scopus 로고
    • For selected examples of trapping when using allylstannanes, see
    • For selected examples of trapping when using allylstannanes, see
  • 47
    • 0003155739 scopus 로고
    • For examples of trapping with other nucleophiles, see:,; see also refs. [17] and [18].
    • For examples of trapping with other nucleophiles, see:, S. D. Rychnovsky, D. J. Skalitzky, Synlett 1995, 555-556; see also refs. [17] and [18].
    • (1995) Synlett , pp. 555-556
    • Rychnovsky, S.D.1    Skalitzky, D.J.2
  • 52
    • 0000516559 scopus 로고
    • Methylene-γ-lactols have been obtained when using α-bromo acetals derived from 2-chloroethanol and from which the chloroethyl group could be removed with sodium in THF/ammonia, see.
    • Methylene-γ-lactols have been obtained when using α-bromo acetals derived from 2-chloroethanol and from which the chloroethyl group could be removed with sodium in THF/ammonia, see:, G. Stork, Jr., R. Mook, J. Am. Chem. Soc. 1983, 105, 3720-3722.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3720-3722
    • Stork Jr., G.1    Mook, R.2
  • 53
    • 79955580666 scopus 로고    scopus 로고
    • For previous studies highlighting the difference in the rate of fragmentation between cyclopropylvinyl and cyclopropylmethyl radicals, see
    • For previous studies highlighting the difference in the rate of fragmentation between cyclopropylvinyl and cyclopropylmethyl radicals, see


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