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For the synthesis of quaternary C-S systems other than thiols asymmetrically, see: Sulfoxides: a) D. A. Evans, G. C. Andews, Acc. Chem. Res. 1974, 7, 147-155;
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sulfides from rearrangement of sulfur ylides: c) X. Zhang, Z. Qu, Z. Ma, W. Shi, X. Jin, J. Wang, J. Org. Chem. 2002, 67, 5621-5625;
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24
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4544298094
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-
note
-
The preparation of a tertiary arylsulfide is described in reference [5a] (53% yield and 85% ee); another one in reference [5b] (43% yield and 10% ee).
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25
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33750456293
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(Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford
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4544388619
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For further development by others, see: T. Kataoka, H. Kinoshita, S. Kinoshita, T. Osamura, S. Watanabe, T. Iwamura, O. Muraoka, G. Tanabe, Angew. Chem. 2003, 115, 2995-2997; Angew. Chem. Int. Ed. 2003, 42, 2889-2891.
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For further development by others, see: T. Kataoka, H. Kinoshita, S. Kinoshita, T. Osamura, S. Watanabe, T. Iwamura, O. Muraoka, G. Tanabe, Angew. Chem. 2003, 115, 2995-2997; Angew. Chem. Int. Ed. 2003, 42, 2889-2891.
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39
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0022413342
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For Lewis acid-assisted cyclization of N-enoyl thioureas leading to 1,3-thiazines, see: M. Dzurilla, P. Kutschy, P. Kristan, Synthesis 1985, 933-934.
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Dzurilla, M.1
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40
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4544278076
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-
note
-
3 led to variable quantities of undesired side products.
-
-
-
-
41
-
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4544357711
-
-
CCDC-228804 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
-
-
-
-
42
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4544320956
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note
-
Mixtures of different E/Z composition were obtained by either column chromatography- or recrystallization-driven enrichment of the original E/Z mixture. See Supporting Information for details.
-
-
-
-
43
-
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0035891621
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For example, it has been described recently that the conjugate addition of lithium thiophenolate to an E and Z mixture of a cyclic enone gives exclusively one diastereomeric addition product. T. J. Houghton, C. Soongyu, V. H. Rawal, Org. Lett. 2001, 3, 3615-3617.
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44
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4544334342
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note
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Note for this case it is the opposite configuration of both the auxiliary and the resulting tertiary sulfanyl. Also, see reference [25].
-
-
-
-
45
-
-
0037696083
-
-
and references therein
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The synthesis of β,β-disubstituted Michael acceptors with either solely E or solely Z configuration is, in general, not so straightforward. For further information, see, for instance, N. Zhu, D. G. Hall, J. Org. Chem. 2003, 68, 6066-6069, and references therein.
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Zhu, N.1
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46
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4544294566
-
-
note
-
There are two possible rationales: kinetic production of the observed diastereomer through any reaction pathway involving a common intermediate reachable from both E- and Z-configured enoyl derivatives, and thermodynamic equilibration of the formed diastereomeric products before final hydrolysis. Among the possible pathways for the first rationale would be the virtual E/Z isomerization of the substrate under the reaction conditions. After analysis by NMR spectroscopy of aliquots taken for a set of reactions at times corresponding to different degrees of reaction conversion, however, no detectable E/Z isomerization could be observed, and this possibility can be ruled out.
-
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a) E. Lee, E. J. Jeong, E. J. Kang, L. T. Sung, S. K. Hong, J. Am. Chem. Soc. 2001, 123, 10131-10132;
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4544284407
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note
-
The enantiomer of 10 is obtained in >97% ee from the reduction of 7 under otherwise identical conditions.
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-
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