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1
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4344610661
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For reviews, see:
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For reviews, see:. Castro A.M.M. Chem. Rev. 104 (2004) 2939-3002
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(2004)
Chem. Rev.
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Castro, A.M.M.1
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3
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0037041597
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Chai Y., Hong S.-P., Lindsay H.A., McFarland C., and McIntosh M.C. Tetrahedron 58 (2002) 2905-2928
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(2002)
Tetrahedron
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Chai, Y.1
Hong, S.-P.2
Lindsay, H.A.3
McFarland, C.4
McIntosh, M.C.5
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5
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33747802179
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For some examples of recent leading works on Claisen rearrangement and related reactions, see:
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15
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0000967977
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Mulder J.A., Hsung R.P., Frederick M.O., Tracey M.P., and Zificsak C.A. Org. Lett. 4 (2002) 1383-1386
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(2002)
Org. Lett.
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Mulder, J.A.1
Hsung, R.P.2
Frederick, M.O.3
Tracey, M.P.4
Zificsak, C.A.5
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20
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33747770791
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For selected works, see:
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25
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3042539752
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Yamamoto H. (Ed), Oxford, New York, NY Chapter 2
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Maruoka K. In: Yamamoto H. (Ed). Lewis Acid Reagents (1999), Oxford, New York, NY 5-29 Chapter 2
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(1999)
Lewis Acid Reagents
, pp. 5-29
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Maruoka, K.1
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39
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0001423835
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For a mechanistic discussion, see:
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For a mechanistic discussion, see:. Gajewski J.J. Acc. Chem. Res. 30 (1997) 219-225
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(1997)
Acc. Chem. Res.
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Gajewski, J.J.1
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41
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33747761381
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For some examples of works on Lewis acid-mediated [1,3] rearrangement of allyl vinyl ethers, see:
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46
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33747772831
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note
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Yamamoto and Maruoka briefly mentioned in their paper that these bulky organo aluminum-mediated Claisen rearrangements do not entirely proceed through a [3,3] concerted pathway: certain substrates, such as 1-phenyl-2-propenyl vinyl ether 3b, undergo the [1,3] rearrangement in competition to the normal [3,3] Claisen rearrangement (see Refs. 5b,c,e).
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48
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33747792160
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We have developed porphyrin-based Lewis acid catalysts that can promote regio- and stereoselective isomerization of epoxides to carbonyl compounds, see:
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51
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33747771837
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Several synthetically useful metalloporphyrin-catalyzed reactions have recently been reported:
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59
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0345664754
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Jacobsen et al. reported that chromium and manganese salen complexes are useful Lewis acid catalysts for stereoselective ring-opening reactions of epoxides:
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Jacobsen et al. reported that chromium and manganese salen complexes are useful Lewis acid catalysts for stereoselective ring-opening reactions of epoxides:. Martinez L.E., Leighton J.L., Carsten D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897-5898
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(1995)
J. Am. Chem. Soc.
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Martinez, L.E.1
Leighton, J.L.2
Carsten, D.H.3
Jacobsen, E.N.4
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60
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33747798132
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note
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With lower catalyst loading, the rearrangements proceeded with impractically slow rate along with reduced E/Z selectivity. For example, the rearrangement of 1a with 2 mol % of Cr(TPP)Cl under the same reaction conditions did not complete over 24 h to give a 1:1 mixture of E- and Z-2a in 63% yield.
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66
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33747783695
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note
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It is well known that simple thermal Claisen rearrangements of aliphatic allyl vinyl ethers are highly stereoselective, leading almost exclusively to the E-configuration of the newly created double bond (see Refs. 1a, 5c, d, and 12).
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67
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0033574393
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Malkov A.V., Baxendale I.R., Dvořak D., Mansfield D.J., and Kočovsky P. J. Org. Chem. 64 (1999) 2737-2750
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J. Org. Chem.
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Malkov, A.V.1
Baxendale, I.R.2
Dvořak, D.3
Mansfield, D.J.4
Kočovsky, P.5
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70
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37049092088
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Jemison R.W., Laird T., Ollis W.D., and Sutherland I.O. J. Chem. Soc., Perkin Trans. 1 (1980) 1450-1457
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(1980)
J. Chem. Soc., Perkin Trans. 1
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Jemison, R.W.1
Laird, T.2
Ollis, W.D.3
Sutherland, I.O.4
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