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See Supporting Information
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See Supporting Information.
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21
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20544435638
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note
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The (E)-meso-enediol was also observed to a lesser extent (∼9%, ref 7b), but the corresponding enediol was not observed in our dimerization of tert-butyloxirane.
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22
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0033603429
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For examples of the uses of symmetric 2-ene-1,4-diols in total synthesis, see: (a) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40, 4829-4832.
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20544448402
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note
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2; EtOAc/petrol) to give the enediols.
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31
-
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20544447907
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note
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LTMP precipitated from the hexane/t-BuOMe mixture; however, upon addition of the epoxide, the solution became homogeneous (this did not occur at higher reaction concentrations and was detrimental to the yield).
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32
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0037138704
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Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
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33
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20544444152
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note
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The (E)-olefin geometry of 3a was confirmed by X-ray crystallography; see Supporting Information.
-
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-
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34
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0346157330
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20544437587
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note
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The (E)-olefin geometry of 6 was confirmed by comparison with an authentic sample synthesized by 1,6-bis-trityl protection of (E)-3,4-dideoxy-D-mannitol (ref 14a).
-
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-
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36
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0346051195
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Made by deprotonation of the corresponding commercially available amine with n-BuLi/TMEDA (1:1); see: Kopka, I. E.; Fataftah, Z. A.; Rathke, M. W. J. Org. Chem. 1987, 52, 448-450.
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20544462521
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note
-
Under these conditions this base remains in solution, whereas LTMP precipitates, which results in longer reaction times and diminished yields. Application of these conditions to (R)-cyclohexyl oxirane did not lead to an improvement in yield or E:Z selectivity.
-
-
-
-
40
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20544459754
-
-
note
-
2O)).
-
-
-
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41
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0001081924
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For an asymmetric synthesis of D-altritol based on a related strategy, see: Evans, P. A.; Murthy, V. S. J. Org. Chem. 1998, 63, 6768-6769.
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0037111592
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Stemp, G.8
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44
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20544437345
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note
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2O)).
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