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(c) Comins, D. L.; Joseph, S. P.; Hong, H.; Al-awar, R. S.; Foti, C. J.; Zhang, Y. M.; Chen, X.; Lamunyon, D. H.; Guerra-Weltzien, M. Pure & Appl. Chem., 1997, 69, 477-481.
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(a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem., 1997, 62, 2555-2563.
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(b) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Portonovo, P. S. Tetrahedron Lett., 1993, 34, 6229-6232.
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0011383755
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Refluxing (Z)-4-chloro-but-2-en-1-ol with sodium salt of sulfinic acid in MeOH for 8 h afforded 1 in 60% yield. (Z)-4-Chloro-but-2-en-1-ol was prepared from cis-but-2-en-1-ol following the procedure of
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Refluxing (Z)-4-chloro-but-2-en-1-ol with sodium salt of sulfinic acid in MeOH for 8 h afforded 1 in 60% yield. (Z)-4-Chloro-but-2-en-1-ol was prepared from cis-but-2-en-1-ol following the procedure of Colonge, J.; Poilane, G. Bull. Soc. Chim, Fr., 1955, 953-955.
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Colonge, J.1
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0345339994
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(a) ed. by Baldwin, J. E.; Magnus, P. D., Pergamon Press, Oxford, Chap. 3
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(a) Simpkins, N. S. Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series, ed. by Baldwin, J. E.; Magnus, P. D., Pergamon Press, Oxford, 1993, Vol. 10. Chap. 3.
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Simpkins, N.S.1
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0025865630
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(b) For an excellent review on dianion chemistry see
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(b) For an excellent review on dianion chemistry see: Thompson, C. M.; Green, D. L. C. Tetrahedron, 1991, 47, 4223-4285.
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31
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0345339993
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note
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Studies were not done to improve the selectivity. However, 2.2 equiv. of LDA instead of LiHMDS under similar conditions afforded 3a as a single diastereomer (95%) in 30% yield.
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32
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0344046175
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note
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+, calculated value=470.14598).
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34
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0022793963
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(b) (c) See Ref. 8a
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(b) Gais, H.-J.; Vollhardt, J.; Lindner, H. J. Angew, Chem. Int. Ed. Engl. 1986, 25, 939-941. (c) See Ref. 8a.
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37
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0344046172
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note
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3N to obtain completely the cyclized compound after purification.
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38
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0344908836
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note
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+, calculated value=314.12148).
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39
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0345339989
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NOE details
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NOE details:
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40
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0345339988
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note
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3P (1.4 equiv.) in THF under an argon atmosphere and after 15 min 4f (1 equiv. in THF) was added at -10°C. The mixture was slowly warmed to RT and then stirred for 12 h. The solvent was removed under reduced pressure and the residue was chromatographed in a silica gel flash column using EtOAc and then 5% MeOH in EtOAc.
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41
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49549126692
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85093693595
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(d) Genission, Y.; Mehmandoust, M. Marazano, C.; Das, B. C. Heterocycles, 1994, 39, 811-818.
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46
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(e) Quan, P. M.; Karns, T. K. B.; Quin, L. D. J. Org. Chem., 1965, 30, 2769-2772.
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