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Volumn 67, Issue 24, 2002, Pages 8351-8359

Synthesis of allylic alcohols from oxazolinyloxiranes

Author keywords

[No Author keywords available]

Indexed keywords

RING OPENING;

EID: 0037195715     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026234d     Document Type: Article
Times cited : (9)

References (50)
  • 33
    • 0001449812 scopus 로고
    • CH2-H ∼ 0 Hz) between the oxirane β-hydrogen and the carbon of the methylene group (or of the methyl group) of the substituent on the α-carbon, as reported: Kingsbury, C. A.; Durham, D. L.; Hutton, R. J. Org. Chem. 1978, 43, 4696-4700. The configuration to 2h/2i and 5e was assigned either by analogy to similar trisubstituted aryl methyl oxazolinyloxiranes as reported in ref 16 or by analogy to 5d, respectively. The configuration to the inseparable diastereomers 2j could not be assigned.
    • (1978) J. Org. Chem. , vol.43 , pp. 4696-4700
    • Kingsbury, C.A.1    Durham, D.L.2    Hutton, R.3
  • 38
    • 0037039907 scopus 로고    scopus 로고
    • (d) Lithiated 2-chloromethyl-2-oxazoline is an extremely reactive intermediate for undergoing smooth homocoupling reaction to give transbis(oxazolinyl)ethene and trans-1,2,3-tris(oxazolinyl)cyclopropane, as reported: Capriati, V.; Florio, S.; Luisi, R.; Rocchetti, M. T. J. Org. Chem. 2002, 67, 759-763.
    • (2002) J. Org. Chem. , vol.67 , pp. 759-763
    • Capriati, V.1    Florio, S.2    Luisi, R.3    Rocchetti, M.T.4
  • 45
    • 0003409730 scopus 로고
    • Wiley: New York; Chapter 4
    • 3J(CN,H) coupling constants between the iminic carbon and the olefinic proton. In the case of the E isomers (having a cis-type arrangement between the above groups) couplings have been found to be always smaller (7.5-8.5 Hz) than those of the Z ones (10.6-11.5 Hz) as reported for similar π-bonded systems: Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: New York, 1988; Chapter 4, pp 526-543.
    • (1988) Carbon-13 NMR Spectroscopy , pp. 526-543
    • Kalinowski, H.-O.1    Berger, S.2    Braun, S.3
  • 46
    • 0034701307 scopus 로고    scopus 로고
    • LDA is recognized to exist as a disolvated dimer in ethereal solvents (Sun, X.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452-2458), while s-BuLi complexed by TMEDA is usually monomeric going towards an endothermic disproportionation from a 1:1 complex to a 1:2 complex according to the temperature (Catala, J. M.; Clouet, G.; Brossas, J. J. Organomet. Chem. 1981, 219, 139-143).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2452-2458
    • Sun, X.1    Collum, D.B.2
  • 47
    • 2242495636 scopus 로고
    • LDA is recognized to exist as a disolvated dimer in ethereal solvents (Sun, X.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452-2458), while s-BuLi complexed by TMEDA is usually monomeric going towards an endothermic disproportionation from a 1:1 complex to a 1:2 complex according to the temperature (Catala, J. M.; Clouet, G.; Brossas, J. J. Organomet. Chem. 1981, 219, 139-143).
    • (1981) J. Organomet. Chem. , vol.219 , pp. 139-143
    • Catala, J.M.1    Clouet, G.2    Brossas, J.3
  • 48
    • 2242449972 scopus 로고    scopus 로고
    • note
    • The possibility that the lower stereoselection of reactions promoted by LDA could be attributed to an isomerization reaction of Z isomers into E isomers promoted by the formed diisopropylamine can be ruled out. Indeed, Z-8a, Z-8b, and Z-8d do not isomerize to the corresponding E isomers when treated with diisopropylamine and E-8d does not isomerize to Z-8d.
  • 49
    • 2242421202 scopus 로고    scopus 로고
    • note
    • All efforts made in order to separate diastereomers 5d and 5e failed so far.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.