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For general reviews, see: (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
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27
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33748285856
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note
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Premetallated conditions: base added to sulfone, then aldehyde added.
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28
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33748274581
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note
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Barbier conditions: base added to the mixture of sulfone and aldehyde.
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29
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33748264626
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note
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Pent-2-ynyl BT-sulfone, reacting with benzaldehyde according to method A, afforded the corresponding enyne in only 18% yield but with 94:6 Z/E ratio.
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30
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0037087785
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For other examples with high cis-selectivity during the one-pot Julia olefination of allyl benzothiazolyl sulfones with α,β-unsaturated aldehydes, see: (a) Furuichi, N.; Hara, H.; Osaki, T.; Mori, H.; Katsumura, S. Angew. Chem. Int. Ed. 2002, 41, 1023.
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Angew. Chem. Int. Ed.
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Furuichi, N.1
Hara, H.2
Osaki, T.3
Mori, H.4
Katsumura, S.5
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(b) Furuichi, N.; Hara, H.; Osaki, T.; Nakano, M.; Mori, H.; Katsumura, S. J. Org. Chem. 2004, 69, 7949.
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J. Org. Chem.
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Furuichi, N.1
Hara, H.2
Osaki, T.3
Nakano, M.4
Mori, H.5
Katsumura, S.6
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32
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33748286257
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Ref. 13
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Ref. 13.
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33
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13844269070
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(d) Vaz, B.; Alvarez, R.; Souto, J. A.; de Lera, A. R. Synlett 2005, 294.
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Synlett
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Vaz, B.1
Alvarez, R.2
Souto, J.A.3
De Lera, A.R.4
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(e) Vaz, B.; Alvarez, R.; Bruckner, R.; de Lera, A. R. Org. Lett. 2005, 7, 545.
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Org. Lett.
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Vaz, B.1
Alvarez, R.2
Bruckner, R.3
De Lera, A.R.4
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35
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13444283614
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Smith, A. B. III; Freeze, B. S.; LaMarche, M. J.; Hirose, T.; Brouard, I.; Xian, M.; Sundermann, K. F.; Shaw, S. J.; Burlingame, M. A.; Horwitz, S. B.; Myles, D. C. Org. Lett. 2005, 7, 315.
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Org. Lett.
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Smith III, A.B.1
Freeze, B.S.2
Lamarche, M.J.3
Hirose, T.4
Brouard, I.5
Xian, M.6
Sundermann, K.F.7
Shaw, S.J.8
Burlingame, M.A.9
Horwitz, S.B.10
Myles, D.C.11
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36
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33748282215
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manuscript in preparation
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Preparation of aldehyde 8f, starting from the alcohol 9 (Scheme 3). Alcohol 9 was prepared according to: Bonini, C.; Chiummiento, L.; Videtta, V.; Colobert, F.; Solladié, G., manuscript in preparation. (Diagram presented) Scheme 3
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Bonini, C.1
Chiummiento, L.2
Videtta, V.3
Colobert, F.4
Solladié, G.5
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37
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33748277855
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note
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No β-elimination product was observed for aldehyde 8e. Moreover, the optical rotation for the unreacted aldehyde 8f shows the same the value of the starting aldehyde, thus indicating that no epimerization reaction occurs.
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38
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Hayford, A.; Kaloko, J. Jr.; El-Kazaz, S.; Bass, G. Org. Lett. 2005, 7, 2671.
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Org. Lett.
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Hayford, A.1
Kaloko Jr., J.2
El-Kazaz, S.3
Bass, G.4
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