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33745502124
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84989315628
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For recent reviews on quaternary proline derivatives, see: a
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For recent reviews on quaternary proline derivatives, see: (a) Karoyan, P.; Sagan, S.; Lequin, O.; Quancard, J.; Lavielle, S.; Chassaing, G. Tarsets Heterocycl. Syst. 2004, 8, 216-273.
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34250023769
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For an example of ester-enolate Claisen rearrangement in synthesis of quaternary prolines, see: a
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For an example of ester-enolate Claisen rearrangement in synthesis of quaternary prolines, see: (a) Sakaguchi, K.; Yamamoto, M.; Watanabe, Y.; Ohfune, Y. Tetrahedron Lett. 2007, 48, 4821-4824.
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29744470611
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For reviews on Stevens rearrangement, see: (a) Vanecko, J. A.; Wan, H.; West, F. G. Tetrahedron 2006, 62, 1043-1062.
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For the chirality transfer via a chiral borane-amine adduct in alkylation of (S) -N-benzylproline methyl ester, see: Ferey, V.; Vedrenne, P.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 1996, 61, 7244-7245, and references therein.
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For the chirality transfer via a chiral borane-amine adduct in alkylation of (S) -N-benzylproline methyl ester, see: Ferey, V.; Vedrenne, P.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 1996, 61, 7244-7245, and references therein.
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22
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64349114516
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Compound la was prepared from commercially available N, N- dimethyl L-prolineamide.
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Compound la was prepared from commercially available N, N- dimethyl L-prolineamide.
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-
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23
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64349113459
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Similar rearrangement at 60 °C gave 2a in 82% yield and 90:10 er.
-
Similar rearrangement at 60 °C gave 2a in 82% yield and 90:10 er.
-
-
-
-
24
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0001232346
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This is believed to arise from a preferential N pyramidal form, in which the substituent on nitrogen and the C-2 substituent are trans disposed. See: Vedejs, E, Arco, M. J, Powell, D. W, Renga, J. M; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837
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This is believed to arise from a preferential N pyramidal form, in which the substituent on nitrogen and the C-2 substituent are trans disposed. See: Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837.
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33847000590
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For the case with chiral Lewis acid, see: a
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28
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64349112197
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The enantiomeric ratio of 2a was determined by HPLC using a Chiracel OD-H column.
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The enantiomeric ratio of 2a was determined by HPLC using a Chiracel OD-H column.
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29
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44849127029
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For fluorescent anthracene-based amino acid derivatives, see
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-
32
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0034346844
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Only one example of [1, 2]-Stevens rearrangement of an ammonium salt containing a thienylmethyl moiety has been reported. See: Kocharyan, S. T.; Karapetyan, V. E.; Churkina, N. P. Russ. J. Gen. Chem. 2000, 70, 1094-1097.
-
Only one example of [1, 2]-Stevens rearrangement of an ammonium salt containing a thienylmethyl moiety has been reported. See: Kocharyan, S. T.; Karapetyan, V. E.; Churkina, N. P. Russ. J. Gen. Chem. 2000, 70, 1094-1097.
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34
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0028244615
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2O)). See: Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4967-4968.
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2O)). See: Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4967-4968.
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