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1
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66249130893
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Erasmus student from Åarhus University, Denmark
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Erasmus student from Åarhus University, Denmark.
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3
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39
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27144442037
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For recent applications of the cyanoborohydride reduction of enamino esters, see
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For recent applications of the cyanoborohydride reduction of enamino esters, see: (a) Alladoum, J.; Dechoux, L. Tetrahedron Lett. 2005, 46, 8203.
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34547198945
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44
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66249094818
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All compounds described from now on were synthesized in both racemic and enantiomerically pure form. The enantiomeric purity of each intermediate was checked by HPLC on chiral column
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All compounds described from now on were synthesized in both racemic and enantiomerically pure form. The enantiomeric purity of each intermediate was checked by HPLC on chiral column.
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45
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66249133619
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Control experiments showed that cyclization occurred before potassium carbonate workup. Adding sodium hydride before this workup did not improve the yields
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Control experiments showed that cyclization occurred before potassium carbonate workup. Adding sodium hydride before this workup did not improve the yields.
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46
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11844253794
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Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
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47
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0028574724
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48
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0015230701
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49
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66249131238
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In contrast, Blaise reaction with the L-glutamic acid derived amino nitrile led to a mixture of products arizing from both possible cyclizations. Unpublished results
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In contrast, Blaise reaction with the L-glutamic acid derived amino nitrile led to a mixture of products arizing from both possible cyclizations. Zulauf, A.; Alezra, V.; Kouklovsky, C. Unpublished results.
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Zulauf, A.1
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51
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0344875940
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Total synthesis
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(b) Total synthesis: Zhu, J.; Ma, D. Angew. Chem., Int. Ed. 2003, 42, 5348.
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Ma, D.2
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53
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66249131956
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The enantiomeric purity of each of stereoisomers of 38 was determined by HPLC after trifluoroacetylation (see Supporting Information)
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The enantiomeric purity of each of stereoisomers of 38 was determined by HPLC after trifluoroacetylation (see Supporting Information).
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54
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0034741042
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For a discussion about the stereoselectivity of the reduction of related ketones, see: and references therein
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For a discussion about the stereoselectivity of the reduction of related ketones, see: Liang, X.; Andersch, J.; Bols, M. J. Chem Soc., Perkin Trans. 1 2001, 2136, and references therein.
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55
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37049076881
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Heterogeneous hydrogenation of enamino esters
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Heterogeneous hydrogenation of enamino esters: (a) Hashiguschi, S.; Natsugari, H.; Ochiai, M. J. Chem. Soc., Perkin Trans. 1 1988, 2345.
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Rhodium-catalyzed hydrogenation of (Z)-enamino esters: (a) Yan, Y.; Zhang, X. Tetrahedron Lett. 2006, 47, 1567.
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Rhodium-catalyzed hydrogenation of (E)-enamino esters: (a) Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509.
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Ruthenium-catalyzed hydrogenation of enamino esters: Wu, J.; Chen, X.; Guo, R.; Yueng, C.-H.; Chan, A. S. C. J. Org. Chem. 2003, 68, 2490.
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The enantiomeric purity of lactam 42 was determined after conversion into its Fmoc carbamate (see Supporting Information)
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The enantiomeric purity of lactam 42 was determined after conversion into its Fmoc carbamate (see Supporting Information).
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73
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Reviews: Georg Thieme Verlag: Stuttgart
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