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31
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0346952239
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Purchased from Aldrich Chemical Co.
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Purchased from Aldrich Chemical Co.
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33
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43
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85087252921
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note
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2O/AcOH).
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44
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33845281294
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P. Aped, Y. Apeloig, A. Ellencweig, B. Fuchs, I. Goldberg, M. Karni, E. Tartakovsky, J. Am. Chem. Soc. 1987, 109, 1486-1495.
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0346322328
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a) H. Emde, A. Götz, K. Hofmann, G. Simchen, Liebigs Ann. Chem. 1981, 1634-1657;
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Emde, H.1
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0028062130
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33947085849
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K. B. Sharpless, R. F. Lauer, A. Y. Teranishi, J. Am. Chem. Soc. 1973, 95, 6137-6139.
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Sharpless, K.B.1
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F. J. Sardina, M. H. Howard, A. M. P. Koskinen, H. Rapoport, J. Org. Chem. 1989, 54, 4654-4660.
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Sardina, F.J.1
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52
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0001150685
-
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The catalytic system TMSI/HMDS has been used before for the TMS-protection of anilins, see : A. B. Smith III, M. Visnick, J. N. Haseltine, P. A. Sprengeler, Tetrahedron 1986, 42, 2957-2969.
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Smith A.B. III1
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53
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33746494993
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3N, see Y. Ito, T. Hirato, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013). Seagusa et al also observed partial silyl enol ether hydrolysis. In our case, the difference in steric environment apparently favors the dehydrosilylation of the more accessible side chain silyl enol ether while the more hindered cyclic enol ether undergoes acid-catalyzed hydrolysis. 44: Obtained from ketal ketone 32 by deprotonation with one equivalent of base (LiHMDS) under thermodynamic conditions, followed by quenching of the resulting enolate with the powerful electrophile PhSeCl. In this case the cyclic enolate is obviously the thermodynamically most stable species.
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Ito, Y.1
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54
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33847802966
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H. J. Reich, J. M. Renga, I. L. Reich, J. Am. Chem. Soc. 1975, 97, 5434-5447.
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0002497872
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a) D. I. Schuster, G. Lem, N. A. Kaprinidis, Chem. Rev. 1993, 93, 3-22;
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c) M. T. Crimmins, S. W. Marsacarella, L. D. Bredon, Tetrahedron Lett. 1985, 26, 997-1000.
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49249150992
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The direct 1,4-addition of TMSI to enone systems was previously reported: a) R. D. Miller, D. R. McKean, Tetrahedron Lett. 1979, 2305-2308;
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Miller, R.D.1
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61
-
-
0346952232
-
-
note
-
Attempts to remove the TMS protecting group by standard, fluoride-mediated procedures (e. g. HF-py, TBAF) resulted either in the decomposition of the starting material or in numerous polar products.
-
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-
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62
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0346322318
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a) J. M Conia, M. Bortilussi, R. Bloch, Tetrahedron Lett. 1973, 27, 2499-2502;
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Conia, J.M.1
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64
-
-
0347583289
-
-
note
-
During detailed studies we also isolated enol ether 55 as a byproduct (≈4%) from this reaction.
-
-
-
-
65
-
-
0031832945
-
-
and references therein
-
The Brønsted acid catalyzed thermal isomerization of silyl enol ethers was previously reported, see: A. Deyine, G. Dujardin, M. Mammeri, J.-M. Poirier, Synth. Commun. 1998, 28, 1817-1821, and references therein. In our case, the flask walls are apparently acidic enough at the high temperatures used to cause isomerization.
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Deyine, A.1
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66
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37049088336
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M. Ihara, M. Katogi, K. Fukumoto, T. Kametani, J. Chem. Soc. Perkin Trans, 1 1988, 2963-2970.
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Ihara, M.1
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Kametani, T.4
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67
-
-
85087252886
-
-
note
-
2, toluene and ether were obtained from Fischer Scientific.
-
-
-
-
68
-
-
85087252681
-
-
note
-
n (1.0 g) and phosphomolybdic acid (1.5 g).
-
-
-
-
69
-
-
84985591654
-
-
The procedure presented here was originally expected to provide hydroxymethylation of lactide 14. See also: B. M. Trost, A. S. Tasker, G. Rüther, A. Brandes, J. Am. Chem. Soc. 1991, 113, 670-672.
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Trost, B.M.1
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Rüther, G.3
Brandes, A.4
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70
-
-
0347583290
-
-
note
-
Alternatively, on a large scale, diketo dilactones 28a/b could be purified by trituration in warm ether.
-
-
-
-
71
-
-
0348212950
-
-
note
-
Caution: This reaction proved very scale-dependent and sensitive!
-
-
-
|