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Volumn 24, Issue 28, 1983, Pages 2865-2868

Erythroselectivity in addition of γ-substituted allylsilanes to aldehydes in the presence of titanium chloride

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EID: 0000234052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)88045-4     Document Type: Article
Times cited : (110)

References (27)
  • 1
    • 0000344737 scopus 로고
    • Oraganometallic Compounds for Stereoregulated Synthesis of Acyclic Systems. Their Application to the Synthesis of the Prelog-Djerassi Lactonic Acid
    • For review, see
    • (1982) HETEROCYCLES , vol.18 , pp. 357
    • Yamamoto1    Maruyama2
  • 10
    • 0006448547 scopus 로고
    • Stereoselective acyclic synthesis via allylmetals: An efficient synthesis of (.+-.)-4-methylheptan-3-ol, an aggregation pheromone of the smaller european elm bark beetle.
    • (1982) Chemistry Letters , pp. 1297
    • Koreeda1    Tanaka2
  • 11
    • 0002615295 scopus 로고
    • Stereoselective acyclic synthesis via allylmetals: Structural dependence in a Lewis-acid catalyzed addition of allyltins to aldehydes.
    • (1982) Chemistry Letters , pp. 1299
    • Koreeda1    Tanaka2
  • 13
    • 49549128832 scopus 로고
    • Reports including reaction of γ-substituted allylsilanes with aldehydes in the presence of a Lewis acid have appeared, but they have not referred to the stereochemistry of the products:
    • (1976) Tetrahedron Lett. , pp. 1295
    • Hosomi1    Sakurai2
  • 15
    • 33847085986 scopus 로고
    • has described in the footnote that titanium chloride mediated reaction of crotyltrimethylsilane with propanal produced a mixture of erythro (60%) and threo (40%) isomers.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7107
    • Yamamoto1    Yatagai2    Naruta3    Maruyama4
  • 16
    • 84918678077 scopus 로고
    • Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides
    • For reviews concerning nickel-catalyzed Grignard cross-coupling, see
    • (1980) Pure and Applied Chemistry , vol.52 , pp. 669
    • Kumada1
  • 18
    • 0011229760 scopus 로고
    • Isomerically pure (E)-bromopropene (2a) was obtained as follows: Commercially available 1-bromopropene (50 g, 0.41 mol) consisting of E (30%) and Z (70%) isomers was added to sodium hydroxide (12 g, 0.30 mol) in 200 ml of butanol. The mixture was heated under reflux (for ca. 40 h) until no (Z-isomer was detected by GLC. Distillation, bp 65°C) through a column (25 cm) packed with glass helices gave 9.5 g (63%) of (E)-2a, which must be stored in the dar. (Z)-2a was prepared according to the reported procedure:
    • (1933) J. Am. Chem. Soc. , vol.55 , pp. 4279
    • Bachman1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.