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1
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4344610661
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For a recent, comprehensive review of the Claisen rearrangement, see: A.M.M. Castro Chem. Rev. 104 2004 2939
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Chem. Rev.
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Castro, A.M.M.1
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3
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13244259829
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(b) For a recent review of the Ireland-Claisen rearrangement, and leading references, see: M.C. McIntosh Tetrahedron 58 2002 2905
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(2002)
Tetrahedron
, vol.58
, pp. 2905
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McIntosh, M.C.1
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5
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0034603016
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(a) For Ireland-Claisen rearrangements of silyl ketene acetals derived from simple methyl allyl malonates involving desilylation and decarboxylation in a separate step, see: C. Fehr, and J. Galindo Angew. Chem., Int. Ed. 39 2000 569
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Angew. Chem., Int. Ed.
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Fehr, C.1
Galindo, J.2
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6
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4043177166
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(b) For recent examples of regio- and enantioselective metal-catalysed decarboxylative allylation reactions, see: E.C. Burger, and J.A. Tunge Org. Lett. 6 2004 2603
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(2004)
Org. Lett.
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Burger, E.C.1
Tunge, J.A.2
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9
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18744415432
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(e) For a review of transition metal-catalysed decarboxylative additions of enolates, see: J.A. Tunge, and E.C. Burger Eur. J. Org. Chem. 2005 1715
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Eur. J. Org. Chem.
, pp. 1715
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Tunge, J.A.1
Burger, E.C.2
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10
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13244296835
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Parts of this work have been communicated in preliminary form: (a) D. Bourgeois, D. Craig, N.P. King, and D.M. Mountford Angew. Chem., Int. Ed. 44 2005 618
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Bourgeois, D.1
Craig, D.2
King, N.P.3
Mountford, D.M.4
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13
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28944451141
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Purchased from Aldrich Chemical Co.
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Purchased from Aldrich Chemical Co.
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23
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0344083335
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(b) For recent applications of the Carroll rearrangement in synthesis, see: M. Defosseux, N. Blanchard, C. Meyer, and J. Cossy Org. Lett. 5 2003 4037
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(2003)
Org. Lett.
, vol.5
, pp. 4037
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Defosseux, M.1
Blanchard, N.2
Meyer, C.3
Cossy, J.4
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25
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0037128390
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(d) For a review, including an account of asymmetric Carroll rearrangements, see: A. Job, C.F. Janeck, W. Bettray, R. Peters, and D. Enders Tetrahedron 58 2002 2253
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(2002)
Tetrahedron
, vol.58
, pp. 2253
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Job, A.1
Janeck, C.F.2
Bettray, W.3
Peters, R.4
Enders, D.5
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30
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28944445637
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unpublished results.
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We have found subsequently that two equivalents of the mixed malonate conjugate base are generally sufficient for efficient tosylation with TsF: Paina, F., unpublished results.
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Paina, F.1
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31
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28944453859
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note
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Compounds 12d and 12h were formed as 70:30 mixtures of diastereoisomers; compound 12i was formed as a 61:39 mixture of diastereoisomers. Major isomers have not been assigned in these cases.
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32
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28944441622
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note
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Yields cited for 11 are based on tosyl fluoride; yields in parentheses are for recovered 10 and are calculated from the total recoverable amount based on the yield of 11 and the amount of 10 used (4.5 equiv with respect to TsF). For example, a 70% yield of 11 means the total recoverable amount of 10 is (4.5-0.7)=3.8 equiv; 74% recovery means that (0.74×3.8=2.81 equiv) of 10 was recovered.
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84943055026
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N. Ono, T. Yoshimira, T. Saito, R. Tamura, R. Tanikaga, and A. Kaji Bull. Chem. Soc. Jpn. 52 1979 1716
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Bull. Chem. Soc. Jpn.
, vol.52
, pp. 1716
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Ono, N.1
Yoshimira, T.2
Saito, T.3
Tamura, R.4
Tanikaga, R.5
Kaji, A.6
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