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Tetrahedron Letters
Volumn 20, Issue 22, 1979, Pages 2043-2046
A novel synthesis of α-methylene-γ-butyrolactones from 1-(N,N-dimethylaminomethyl)cyclopropanecarboxylate esters
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Indexed keywords

EID: 0042588634     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)86258-4     Document Type: Article
Times cited : (18)
References (26)
  • 11
    • 0001705176 scopus 로고
    • Stereoselective Monoalkylation of α-Halocyclopropyllithiums. A Versatile Method for the Synthesis of α-Alkylcyclopropyl Acetates and Alkylidenecyclopropanes
    • The isomer is 1-r-bromo-1-(N,N-dimethylaminomethyl)-2-c-hexylcyclopropane. The observed stereoselectivity is consistent with the results obtained in thermodynamically controlled generation of the lithium carbenoid. See
    • (1977) Bulletin of the Chemical Society of Japan , vol.50 , pp. 3288
    • Kitatani1    Hiyama2    Nozaki3
  • 12
  • 13
    • 84918355501 scopus 로고    scopus 로고
    • In some cases IV was produced to some extent (less than 40% yield as estimated by PMR) during trimethylsilyl iodide treatment. However, transformation of the desired product was effectively executed by the subsequent thermolysis.
  • 14
    • 84918355500 scopus 로고    scopus 로고
    • (a) All the products are characterized analytically and spectrometrically. (b) Lithiation of IIa with n-BuLi. (c) Contained 12% of the stereoisomer. See note 7. (d) Contained 12% of the regioisomer. See text.
  • 15
    • 84918355499 scopus 로고    scopus 로고
    • When stereochemically pure sample of IIIb was subjected to the reaction conditions, the product ratio was a little improved (91% and 9% respectively).
  • 17
    • 0000792398 scopus 로고
    • + + 2). 7-exo-Methoxycarbonyl-7-endo-(N,N-dimethylaminomethyl)norcarane (IIIc). A pentane solution (2.3 M) of [[Truncated]]
    • (1965) J. Org. Chem. , vol.30 , pp. 3475
    • Marshall1    Cohen2
  • 18
    • 0002159802 scopus 로고
    • The initial phase of the reaction would be N-trimethylsilyl ammonium formation which is followed by trimethylsilyl-methyl exchange. Similar phenomenon is observed in
    • (1978) Tetrahedron lett. , pp. 3085
    • Minamikawa1    Brossi2
  • 19
    • 84918355498 scopus 로고    scopus 로고
    • This compound was prepared from IIc and benzyl chloroformate by the standard procedure noted herein, or alternatively from IIIc by ester exchange reaction.
  • 24
    • 0001347256 scopus 로고
    • Über Glykoside mit lacton-bildendem Aglykon, II. Über die Struktur der antibiotisch aktiven Substanzen der Tulpe (Tulipa gesneriana L.)
    • Cf.
    • (1969) Chemische Berichte , vol.102 , pp. 2057
    • Tschesche1    Kämmerer2    Wulff3
  • 25
    • 84918355497 scopus 로고    scopus 로고
    • The amino ester VIII was prepared according to the following scheme:
  • 26
    • 84918355496 scopus 로고    scopus 로고
    • We thank the Ministry of Education, Science and Culture, Japanese Government, for partial financial support (Grant-in-Aid No. 303023).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.