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Volumn 74, Issue 1, 2009, Pages 470-473

General method for the synthesis of phenyliodonium ylides from malonate esters: Easy access to 1,1-cyclopropane diesters

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; CONVENIENT ALTERNATIVES; COPPER CATALYSES; DIAZO COMPOUNDS; DIESTERS; DIMETHYL MALONATE; GENERAL METHODS; IODONIUM; MALONATE; MALONATES; SYNTHESIS OF;

EID: 58149311064     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802208q     Document Type: Article
Times cited : (102)

References (52)
  • 1
    • 15644378136 scopus 로고
    • For excellent reviews on the chemistry of electrophilic cyclopropanes, see: a
    • For excellent reviews on the chemistry of electrophilic cyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
    • (1989) Chem. Rev , vol.89 , pp. 165
    • Wong, H.N.C.1    Hon, M.-Y.2    Tse, C.-W.3    Yip, Y.-C.4    Tanko, J.5    Hudlicky, T.6
  • 14
    • 33744462643 scopus 로고    scopus 로고
    • For examples of cyclopropanations using iodonium ylides, see: (a) Müller, P; Allenbach, Y. F, Chappelet, S, Ghanem, A. Synthesis 2006, 1689
    • For examples of cyclopropanations using iodonium ylides, see: (a) Müller, P; Allenbach, Y. F.; Chappelet, S.; Ghanem, A. Synthesis 2006, 1689.
  • 29
    • 85033148217 scopus 로고
    • and references cited therein
    • (p) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431, and references cited therein.
    • (1990) Synthesis , pp. 431
    • Moriarty, R.M.1    Vaid, R.K.2
  • 44
    • 58149294089 scopus 로고    scopus 로고
    • Concentration at higher temperature gave significantly lower yields
    • Concentration at higher temperature gave significantly lower yields.
  • 45
    • 58149280904 scopus 로고    scopus 로고
    • Since these side products are generally formed in the subsequent reaction, they do not interfere in the cyclopropanation reaction. Indeed, no significant difference in the yields were observed in cyclopropanation when the crude ylide was used
    • Since these side products are generally formed in the subsequent reaction, they do not interfere in the cyclopropanation reaction. Indeed, no significant difference in the yields were observed in cyclopropanation when the crude ylide was used.
  • 46
    • 58149314634 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 47
    • 58149296616 scopus 로고    scopus 로고
    • The iodonium ylide of the Meldrum's acid is an exception since it is stable at room temperature for many weeks
    • The iodonium ylide of the Meldrum's acid is an exception since it is stable at room temperature for many weeks
  • 48
    • 58149288724 scopus 로고    scopus 로고
    • Müller and Hadjiarapoglou have reported the synthesis of this iodonium ylide in 56 and 61% yield respectively (see refs 5f and 5o).
    • Müller and Hadjiarapoglou have reported the synthesis of this iodonium ylide in 56 and 61% yield respectively (see refs 5f and 5o).
  • 49
    • 58149290302 scopus 로고    scopus 로고
    • Five percent yield was obtained when MgO was added
    • Five percent yield was obtained when MgO was added.
  • 51
    • 58149280905 scopus 로고    scopus 로고
    • 6 complex was used.
    • 6 complex was used.
  • 52
    • 58149288725 scopus 로고    scopus 로고
    • esp = α,α,α′,α′-Tetramethyl-1,3- benzenedipropanoate.
    • esp = α,α,α′,α′-Tetramethyl-1,3- benzenedipropanoate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.