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Volumn 12, Issue 11, 2010, Pages 2464-2467

Activation of Fmoc-protected N, O-acetals using trimethylsilyl halides: Mechanistic and synthetic studies

Author keywords

[No Author keywords available]

Indexed keywords

9 FLUORENYLMETHOXYCARBONYL; 9-FLUORENYLMETHOXYCARBONYL; ACETAL DERIVATIVE; FLUORENE DERIVATIVE; HALOGENATED HYDROCARBON; TRIMETHYLSILYL DERIVATIVE;

EID: 77952983891     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100494z     Document Type: Article
Times cited : (6)

References (44)
  • 1
    • 77953018643 scopus 로고    scopus 로고
    • For references related to the Fmoc protecting group, see
    • For references related to the Fmoc protecting group, see
  • 4
    • 77952998442 scopus 로고    scopus 로고
    • For an overview of solid-phase peptide synthesis, see
    • For an overview of solid-phase peptide synthesis, see
  • 6
    • 77952985927 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see
  • 9
    • 0001673091 scopus 로고
    • 1 st ed.; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, UK
    • Hiemstra, H.; Speckamp, W. N. Comprehensive Organic Synthesis, 1 st ed.; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, pp 1047 - 1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 15
    • 77952972739 scopus 로고    scopus 로고
    • For the first report of a TMSCl activation approach to Pictet-Spengler reactions, see
    • For the first report of a TMSCl activation approach to Pictet-Spengler reactions, see
  • 17
    • 77952962886 scopus 로고    scopus 로고
    • For a related opening of a cyclic acetal using dialkylboron bromide, see
    • For a related opening of a cyclic acetal using dialkylboron bromide, see
  • 22
    • 77952967827 scopus 로고    scopus 로고
    • See the supporting information
    • See the supporting information.
  • 30
    • 77953008111 scopus 로고    scopus 로고
    • note
    • halomethylcarbamates 2, and the other halomethylcarbamates described herein, can can be isolated, though they are very sensitive to moisture and are less pure upon isolation than they were in situ. Thus, we prefer to avoid handling the halomethylcarbamate compounds directly.
  • 31
    • 77952960085 scopus 로고    scopus 로고
    • For selected recent examples, see
    • For selected recent examples, see
  • 42
    • 77952986224 scopus 로고    scopus 로고
    • note
    • The dependence on the concentration of enamine is also consistent with rate-limiting addition of the enamine to an acyliminium ion, which cannot be discounted but seems unlikely.
  • 43
    • 77953004822 scopus 로고    scopus 로고
    • For a study of enamine nucleophilicity, see
    • For a study of enamine nucleophilicity, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.