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Tetrahedron Letters
Volumn 26, Issue 2, 1985, Pages 139-142
Stereospecific synthesis of enamines from α,β-epoxysilanes
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Indexed keywords

EID: 0000321839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)61863-4     Document Type: Article
Times cited : (17)
References (33)
  • 1
    • 0000177180 scopus 로고
    • For a comprehensive review of enamines, see
    • (1982) Tetrahedron , vol.38 , pp. 1975-2050
    • Hickmott1
  • 3
    • 0345177510 scopus 로고
    • Two methods for the stereospecific synthesis of enamines have been reported. Diastereomeric mesitoate esters of amino alcohols (resulting from the reactions of cis-and trans-stilbene oxide with morpholine) were each treated with KOtBu in DMSO to give Z (pure) and E (75% E) trisubstituted enamines, respectively:
    • (1965) J. Org. Chem. , vol.30 , pp. 3705-3710
    • Munk1    Kim2
  • 4
    • 0038904964 scopus 로고
    • A number of cis trans primary enamines have been prepared by retro-Diels-Alder reactions:
    • (1980) Tetrahedron , vol.36 , pp. 2497-2503
    • Ripoll1    Lebrun2    Thuillier3
  • 5
    • 0001878611 scopus 로고
    • Base-catalyzed isomerizations of allylamines to enamines have been shown to generate predominantly cis enamines; in some cases cis enamines in up to ∼90% purity have been isolated.
    • (1966) Tetrahedron Lett. , pp. 2863-2866
    • Sauer1    Prahl2
  • 6
    • 84951509137 scopus 로고
    • Basenkatalysierte Doppelbindungs-Isomerisierungen, II. Synthese einfachercis-Enamine
    • (1969) Chemische Berichte , vol.102 , pp. 1917-1927
    • Sauer1    Prahl2
  • 12
    • 85065669957 scopus 로고
    • 3-Metallierte Enamine, III1. Metallierung von 3- und 1-(N-Methylanilino)-propen
    • (1974) Synthesis , pp. 672-674
    • Ahlbrecht1    Eichler2
  • 24
    • 84914404257 scopus 로고    scopus 로고
    • The IR, NMR, and mass spectra were in agreement with the structure of this compound.
  • 25
    • 84914404256 scopus 로고    scopus 로고
    • A preliminary experiment suggests that the α-amino-β-hydroxysilane 3a and the trans epoxide 2 can be separated by extraction with dilute acid.
  • 26
    • 84951509137 scopus 로고
    • Basenkatalysierte Doppelbindungs-Isomerisierungen, II. Synthese einfachercis-Enamine
    • To ascertain the stereochemical purity of the enamines, the most useful peaks in the NMR spectra were those of the olefinic hydrogens α to nitrogen: 4a, δ 5.68 (d, J = 9 Hz); 5a δ 6.02 (d, J = 13.5 Hz); 4b δ 5.41 (d, J = 8.5 Hz) 5b δ 5.73 (d, J = 14 Hz) For additional NMR data on other cis and trans enamines
    • (1969) Chemische Berichte , vol.102 , pp. 1917-1927
    • Sauer1    Prahl2
  • 29
    • 33947329969 scopus 로고
    • Cis enamines with additional conjugating substituents (such as those with the nitrogen in an aromatic ring) or in some cases with the nitrogen in a ring containing additional heteroatoms appear to be considerably more stable than the simple cis enamines reported here. For examples, see
    • (1968) J. Org. Chem. , vol.33 , pp. 212-215
    • Stern1    Krause2
  • 33
    • 37049129490 scopus 로고
    • Studies in mass spectrometry. Part XII. Mass spectra of enamines
    • Preliminary experiments indicate that methanol/alumina and thiophenol/alumina also react with the cis epoxide much faster than with the trans, indicating the potential for preparing isomerically pure enol ethers or vinyl sulfides from a cis/trans mixture of α,β-epoxysilanes.
    • (1966) Journal of the Chemical Society B: Physical Organic , pp. 940-946
    • Jakobsen1    Lawesson2    Marshall3    Schroll4    Williams5

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.