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Silyl-modified Prins cyclization and the silyl-modified Sakurai cyclization are in fact the same reaction, and the name silyl Prins is adopted herein. See: (a) Marko, I. E.; Bayston, D. J. Tetrahedron 1994, 50, 7141.
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33645393961
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note
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Optimum solvent was THF, affording 85:15 selectivity in favor of the desired (Z)-7 (69%). The (Z)-configuration of 7 is crucial for the formation of dihydropyran 3, as elimination of the trimethylsilyl group from the resultant six-membered ring formed from the (E)-isomer is very slow (<10% conversion after 12 h).
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33
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0028219545
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0000010197
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38
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18544368524
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Absolute configuration of ent-10 has been assigned by X-ray diffraction of the derived camphanic ester; see: Meilert, K. T.; Clark, G. R.; Groutso, T.; Brimble, M. A. Acta Crystallogr. Sect. E 2005, E61, O6.
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39
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33645417061
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note
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19F NMR after formation of the Mosher ester.
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44
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33645420062
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note
-
Use of a 600 MHz spectrometer was necessary in order to see splitting of the signals.
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45
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85083243520
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For examples of heteroatom-directed Wacker oxidations see: (a) Tsuji, J. Synthesis 1984, 5, 369.
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Tsuji, J.1
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47
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0013311725
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Lai, J.Y.1
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48
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33645406369
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note
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2O.
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