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For examples in total syntheses, see: (a) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290. (b) Christmann, M.; Bhatt, U.; Quitschalle, M.; Claus, E.; Kalesse, M. Angew. Chem., Int. Ed. 2000, 39, 4364-4366. (c) Williams, D. R.; Ihle, D. C.; Plummer, S. V. Org. Lett. 2001, 3, 1383-1386. (d) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638. (e) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
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Williams, D.R.1
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0034605902
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For examples in total syntheses, see: (a) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290. (b) Christmann, M.; Bhatt, U.; Quitschalle, M.; Claus, E.; Kalesse, M. Angew. Chem., Int. Ed. 2000, 39, 4364-4366. (c) Williams, D. R.; Ihle, D. C.; Plummer, S. V. Org. Lett. 2001, 3, 1383-1386. (d) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638. (e) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
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Claus, E.4
Kalesse, M.5
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14
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0035799895
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For examples in total syntheses, see: (a) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290. (b) Christmann, M.; Bhatt, U.; Quitschalle, M.; Claus, E.; Kalesse, M. Angew. Chem., Int. Ed. 2000, 39, 4364-4366. (c) Williams, D. R.; Ihle, D. C.; Plummer, S. V. Org. Lett. 2001, 3, 1383-1386. (d) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638. (e) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
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Williams, D.R.1
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For examples in total syntheses, see: (a) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290. (b) Christmann, M.; Bhatt, U.; Quitschalle, M.; Claus, E.; Kalesse, M. Angew. Chem., Int. Ed. 2000, 39, 4364-4366. (c) Williams, D. R.; Ihle, D. C.; Plummer, S. V. Org. Lett. 2001, 3, 1383-1386. (d) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638. (e) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
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Takahashi, S.1
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For examples in total syntheses, see: (a) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290. (b) Christmann, M.; Bhatt, U.; Quitschalle, M.; Claus, E.; Kalesse, M. Angew. Chem., Int. Ed. 2000, 39, 4364-4366. (c) Williams, D. R.; Ihle, D. C.; Plummer, S. V. Org. Lett. 2001, 3, 1383-1386. (d) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638. (e) Hilli, F.; White, J. M.; Rizzacasa, M. A. Org. Lett. 2004, 6, 1289-1292.
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18244377844
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The appended carboxy substituent significantly attenuates the reactivity of dienes related to 1, thereby rendering a hetero-Diels-Alder strategy to compounds such as 4 currently untenable under numerous Lewis acid catalyzed conditions surveyed
-
The appended carboxy substituent significantly attenuates the reactivity of dienes related to 1, thereby rendering a hetero-Diels-Alder strategy to compounds such as 4 currently untenable under numerous Lewis acid catalyzed conditions surveyed.
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18
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84985644162
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For dioxinone enolate additions to carbonyl compounds, see: Seebach, D.; Misslitz, U.; Uhlmann, P. Chem. Ber. 1991, 124, 1845-1852. For organomagnesium reagents from dioxinones, see: Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron Lett. 2001, 42, 6847-6850. For a photocycloaddition/fragmentation approach to tetrahydropyrones utilizing dioxinones, see: Dritz, J. H.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 5579-5582.
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For dioxinone enolate additions to carbonyl compounds, see: Seebach, D.; Misslitz, U.; Uhlmann, P. Chem. Ber. 1991, 124, 1845-1852. For organomagnesium reagents from dioxinones, see: Vu, V. A.; Berillon, L.; Knochel, P. Tetrahedron Lett. 2001, 42, 6847-6850. For a photocycloaddition/fragmentation approach to tetrahydropyrones utilizing dioxinones, see: Dritz, J. H.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 5579-5582.
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2). (b) Sabitha, G.; Reddy, G. S. K. K.; Rajkumar, M.; Yadav, J. S.; Ramakrishna, K. V. S.; Kunwar, A. C. Tetrahedron Lett. 2003, 44, 7455-7457 (TMSI).
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Kunwar, A.C.6
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18244401761
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1H NMR (500 MHz) NOE experiments
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1H NMR (500 MHz) NOE experiments.
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18244389798
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Lower catalysts loadings (5 and 10 mol %) increase reaction time but do not adversely affect yield or selectivity
-
Lower catalysts loadings (5 and 10 mol %) increase reaction time but do not adversely affect yield or selectivity.
-
-
-
-
33
-
-
0001207667
-
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An alternative mechanism may involve an oxonia-Cope rearrangement of I followed by ring closure; see: (a) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426-3427. (b) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818 and references therein. (c) Roush, W. R.; Dilley, G. J. Synlett 2001, 955-959. Further investigations to probe the operative reaction pathway are ongoing in our laboratory.
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34
-
-
0035891722
-
-
and references therein
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An alternative mechanism may involve an oxonia-Cope rearrangement of I followed by ring closure; see: (a) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426-3427. (b) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818 and references therein. (c) Roush, W. R.; Dilley, G. J. Synlett 2001, 955-959. Further investigations to probe the operative reaction pathway are ongoing in our laboratory.
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0034966749
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An alternative mechanism may involve an oxonia-Cope rearrangement of I followed by ring closure; see: (a) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426-3427. (b) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818 and references therein. (c) Roush, W. R.; Dilley, G. J. Synlett 2001, 955-959. Further investigations to probe the operative reaction pathway are ongoing in our laboratory.
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Dilley, G.J.2
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18244388325
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1H coupling values (J ≥ 10 Hz) indicating a diaxial vicinal proton disposition
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1H coupling values (J ≥ 10 Hz) indicating a diaxial vicinal proton disposition.
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