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6
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0037782653
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note
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Treatment of 4a with 1 equiv of LDA and then 1 equiv of prenyl bromide at 0 °C gives 5 in high yield.
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8
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0027520330
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Keck, G. E.; McHardy, S. F.; Murry, J. A. Tetrahedron Lett. 1993, 34, 6215.
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Keck, G.E.1
McHardy, S.F.2
Murry, J.A.3
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9
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84984169144
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α-Lactams with β-hydrogens can react with bases to produce α,β-unsaturated amides in a second-order reaction. (See for example: Quast, H., Meichsner, G., Seiferling, B. Chem. Ber. 1987, 120, 217-223.) This scenario predicts that the yield of 6 should increase as the concentration of LDA is increased, contrary to observations. Thus, the involvement of α-lactams in the formation of 6 is discounted.
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Quast, H.1
Meichsner, G.2
Seiferling, B.3
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10
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0001343473
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11
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0038120310
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note
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A product was isolated that lacked the ethoxy group and appeared to be the result of intramolecular cyclization between the hydroxamate oxyanion and the ester group to give an isoxazolidine dione.
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12
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0026730538
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Altenburger, J. M.; Mioskowski, C.; d'Orchymont, H.; Schirlin, D.; Schalk, C.; Tarnus, C. Tetrahedron Lett. 1992, 33 5055-5058.
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14
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0038120311
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note
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We have just recently learned that 0.5% methanesulfonic acid in absolute ethanol gives even higher yields of desilylation (80-85%).
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15
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0001235008
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Hoffman, R. V.; Nayyar, N. K.; Chen, W. J. Am. Chem Soc. 1993, 115, 5031.
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