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1
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0000746177
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Trost B.M. (Ed), Pergamon, Oxford Chapter 7.2
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Wipf P. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 7.2
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(1991)
Comprehensive Organic Synthesis
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Wipf, P.1
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7
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33644652968
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Previously, the 1,4-elimination reactions have reported using α,β-unsaturated acetals:
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Previously, the 1,4-elimination reactions have reported using α,β-unsaturated acetals:. Pichon N., Harrison-Marchand A., Toupet L., and Maddaluno J. J. Org. Chem. 71 (2006) 1892
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(2006)
J. Org. Chem.
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, pp. 1892
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Pichon, N.1
Harrison-Marchand, A.2
Toupet, L.3
Maddaluno, J.4
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10
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0037111595
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Bataille C., Bégin G., Guillam A., Lemiègre L., Lys C., Maddaluno J., and Toupet L. J. Org. Chem. 67 (2002) 8054
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(2002)
J. Org. Chem.
, vol.67
, pp. 8054
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Bataille, C.1
Bégin, G.2
Guillam, A.3
Lemiègre, L.4
Lys, C.5
Maddaluno, J.6
Toupet, L.7
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16
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37049079064
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Canepa C., Prandi C., Sacchi L., and Venturello P. J. Chem. Soc., Perkin Trans. 1 (1993) 1875
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(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 1875
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Canepa, C.1
Prandi, C.2
Sacchi, L.3
Venturello, P.4
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0000952950
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A example of 1,4-elimination reaction of 1,4-dialkoxy-(2Z)-butene:
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A example of 1,4-elimination reaction of 1,4-dialkoxy-(2Z)-butene:. Margot C., Matsuda H., and Schlosser M. Tetrahedron 46 (1990) 2425
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(1990)
Tetrahedron
, vol.46
, pp. 2425
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Margot, C.1
Matsuda, H.2
Schlosser, M.3
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33645791244
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For reviews:. Rappoport Z., and Marek I. (Eds), John Wiley & Sons Ltd., Chichester
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For reviews:. Tomooka K. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 2 (2004), John Wiley & Sons Ltd., Chichester 749-828
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(2004)
The Chemistry of Organolithium Compounds
, vol.2
, pp. 749-828
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Tomooka, K.1
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33748742848
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Baldwin J.E., and Williams R.M. (Eds), Pergamon, Manchester Chapter 8
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Clayden J. In: Baldwin J.E., and Williams R.M. (Eds). Organolithiums: Selectivity for Synthesis (2002), Pergamon, Manchester Chapter 8
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(2002)
Organolithiums: Selectivity for Synthesis
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Clayden, J.1
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Trost B.M. (Ed), Pergamon, Oxford Chapter 4.6
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Brückner R. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 6 (1991), Pergamon, Oxford Chapter 4.6
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(1991)
Comprehensive Organic Synthesis
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Brückner, R.1
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33748740783
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note
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4NBr, allyl bromide, benzene, 50% aq NaOH, rt. Details: see Supplementary data.
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33748748088
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note
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Use of sec- or tert-butyllithium instead of n-butyllithium resulted in lower yields due to de-allylation of 1a.
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33748745156
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A similar reaction of 1-allyloxy-4-methoxy-(2E)-undecene [(E)-1a] in ether was found to give a geometric mixture of 2a in a 31% yield [(1Z,3E)/(1Z,3Z) = 6:4] and a complicated diastereomixture of 3a in a 10% yield with the recovery of the starting material in 37% yield.
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2O instead of THF gave almost the same result.
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2 (1 atm), Lindlar-cat., quinoline, EtOAc, rt. Details: see Supplementary data.
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note
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Examples of 1,4-elimination reaction of γ-benzylicoxy-α,β-unsaturated acetals have been reported: see Ref. 3b and c.
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Trost B.M. (Ed), Pergamon, Oxford Chapter 7.3
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Ziegler F.E. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 7.3
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(1991)
Comprehensive Organic Synthesis
, vol.5
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Ziegler, F.E.1
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