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Volumn 44, Issue 13, 1988, Pages 4113-4134

Chemistry of cyclopropylacylsilanes I. α-functionalized acylsilane reagents for the cyclopropanation of electrophilic alkenes

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Indexed keywords


EID: 0001528673     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)86660-6     Document Type: Article
Times cited : (43)

References (64)
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    • Ruthenium-catalyzed synthesis of vinyl carbamates from carbon dioxide, acetylene, and secondary amines
    • For recent examples of the application of acylsilanes in synthesis, see, references cited therein.
    • (1987) The Journal of Organic Chemistry , vol.52 , pp. 314
    • Reich1    Holtan2    Borkowsky3
  • 13
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    • For a review of the photochemistry of acylsilanes see, A. Padwa, Marcel Dekker, New York
    • (1985) Organic Photochemistry , vol.7 , pp. 149-230
    • Dalton1
  • 15
    • 1342317074 scopus 로고
    • Reaction of 1-trimethylsilylcyclopropyllithium derivatives with dichloromethyl methyl ether. A novel synthesis of cyclopropyl silyl ketones.
    • (1986) Chemistry Letters , pp. 177
    • Nakajima1    Miyaji2    Segi3    Suga4
  • 18
    • 0002427539 scopus 로고
    • Transition-metal catalyzed decomposition of aliphatic diazo compounds — New results and applications in organic synthesis
    • For recent reviews, see
    • (1987) Top. Curr. Chem. , vol.137 , pp. 75
    • Maas1
  • 25
    • 85022524053 scopus 로고
    • Reactions of Organic Anions. LXVII1. Catalytic Synthesis of Cyclopropane Derivatives in Aqueous Medium
    • For recent variants of the McCoy reaction, see
    • (1976) Synthesis , pp. 387
    • Jonczyk1    Makosza2
  • 28
    • 84986679983 scopus 로고
    • Alkylation, Acylation, and Cyclopropanation Reactions ofa-Halo Carboxylic Acid Dianions
    • For recent variants of the McCoy reaction, see
    • (1982) Synthesis , pp. 284
    • Johnson1    Bade2
  • 36
    • 84918149060 scopus 로고    scopus 로고
    • 17 for details see the Experimental Section.
  • 44
    • 0347236151 scopus 로고
    • For a discussion of “lithium bonding” and its relationship to hydrogen bonding, see, and references cited therein.
    • (1986) J. Chem. Ed. , vol.63 , pp. 843
    • Sannigrahi1
  • 49
    • 0003170165 scopus 로고
    • For recent studies fo the stereochemical course of the Michael reaction, see
    • (1985) J. Org. Chem. , vol.50 , pp. 3022
    • Heathcock1    Oare2
  • 54
    • 33847087776 scopus 로고
    • 2b has not been observed previously, although an example of the reverse process has been reported by Cohen and Matz
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6900
    • Cohen1    Matz2
  • 57
    • 84918149059 scopus 로고    scopus 로고
    • Note, however, that the 1-methyl substituted cyclopropanccarboxaldehydes 35a,b could not be decarbonylated under similar conditions.
  • 61
    • 84918149058 scopus 로고    scopus 로고
    • Pure bromoacetylsilane 15 could most likely be prepared via low-temperature recrystallizaton according to the procedure described for the purification of the chloro derivative 14.
  • 62
    • 84918149057 scopus 로고    scopus 로고
    • The reaction may also be performed at room temperature for 24 h with similar results.
  • 63
    • 84918149056 scopus 로고    scopus 로고
    • A pure sample of 24a could be obtained in 61% yield via the reaction of the α-bromoacylsilane 15 with 5 equiv of diethyl fumarate following the general procedure.
  • 64
    • 2242465052 scopus 로고
    • METHYLENE KETONES AND ALDEHYDES BY SIMPLE, DIRECT METHYLENE TRANSFER: 2-METHYLENE-1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE
    • (1981) Organic Syntheses , vol.60 , pp. 88
    • Gras1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.