12 For a single example of the approach illustrated in eq. (2) of Scheme 1,
see: T. Taguchi, H. Sasaki, A. Shibuya and T. Morikawa, Tetrahedron
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13 For reviews, see: (a) A. Maercker, Org. React., 1965, 14, 270; (b) B.
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14 For a recent example of metal-catalyzed synthesis of cyclopropanes
bearing a homologated carbonyl group, see: B. M. Trost, A. Breder, B.
M. O’Keefe, M. Rao and A. W. Franz, J. Am. Chem. Soc., 2011, 133,
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15 (a) R. A. Izidore and R. G. Ghirardelli, J. Org. Chem., 1973, 38, 1790;
(b) A. Nelson and S. Warren, Tetrahedron Lett., 1996, 37, 1501; (c) A.
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16 J.-C. Le Menn, A. Tallec and J. Sarrazin, Can. J. Chem., 1991, 69, 761.
17 Reaction of compound 1a with malononitrile in CHCl3 at room
temperature promoted by K2CO3 afforded the Michael adduct 5 in
50% yield, which supports the proposed tandem process illustrated in
eq. 2 of Scheme 1 (see the Supporting Information for experimental
details†).
Notes and references
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18 The yield of compound 3f did not improve when using 18-crown-6 (1
equiv.) as additive.
19 For a recent review, see: T. Marcelli and H. Hiemstra, Synthesis, 2010,
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11 T. den Hartog, A. Rudolph, B. Macia´, A. J. Minnaard and B. L. Feringa,
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7996 | Org. Biomol. Chem., 2011, 9, 7993–7996
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