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Bassendale, A.R.2
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25
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0002092942
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For examples of the directed deprotonation and rearrangement of vinylogous α-alkoxysilanes, see: (a) Mikami, K.; Kishi, N.; Nakai, T. Chem. Lett. 1989, 1683-1686.
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27
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0041647929
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The [1,2]-Wittig rearrangement of [(aryloxy)methyl]silanes has been initiated by deprotonation and affords α-silylbenzyl alcohols. See: Eisch, J. J.; Galle, J. E.; Piotrowski, A.; Tsai, M.-R. J. Org. Chem. 1982, 47, 5051-5056.
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28
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85034128309
-
-
note
-
The starting α-alkoxysilanes were prepared by reaction of the corresponding α-silyl alcohols with allyl or benzyl trichloroimidates in the presence of catalytic quantities of TMSOTf. For details, see the preceding Letter this issue (see ref 8).
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-
-
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29
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0002049382
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[2,3]-Wittig rearrangement of the dessilyl analogue of 1 proceeds with similar (2:1) preference for the erythro product (Schöllkopf, U.; Fellenberger, K.; Rizk, M. Liebigs Ann. Chem. 1970, 734, 106-115).
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Schöllkopf, U.1
Fellenberger, K.2
Rizk, M.3
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30
-
-
85034122219
-
-
note
-
The same reaction sequence applied to 2b provided analogous results.
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-
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31
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85034124301
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Reference 7b
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(a) Reference 7b.
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33
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0031562483
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Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513-3526.
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Kishimoto, S.4
Kobayashi, Y.5
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35
-
-
85034135385
-
-
note
-
While the retro-Brook sequence only gave 21% of the desired α-hydroxysilane, 67% of the silyl ether was also recovered. Presumably this material could be recycled; however, no attempt to optimize the process was made.
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-
-
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37
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85034126585
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-
note
-
2O at room temperature over 16 h. See Supporting Information for more details.
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-
-
-
40
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0011972850
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-
Although we have no direct evidence of any O-silyl products, the 1,3-silyl migration probably takes place via Brook rearrangement (ref 11) of 26 followed by rearrangement of the resulting homoenolate. For similar examples, see: (a) Kuwajima, I. J. Organomet. Chem. 1985, 285, 137-148.
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(d) For a related review, see: Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665-722.
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Ricci, A.5
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0001702008
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0001050524
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