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30444441133
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and references cited therein Reviews on asymmetric organocatalysis:
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33746277515
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For selected examples of enantioselective, cyclic secondary amine catalyzed, Mannich reactions see:
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In some examples the desired products can still be formed in high enantioselectivities see:
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B. List J. Am. Chem. Soc. 2000 122 9336 9337
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0037032312
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Enamines substituted on the nucleophilic carbon were substantially less reactive With cyclohexanone derived morpholino enamine under the same reaction conditions the conversion of the catalyzed reaction after 15 hours was disappointingly 18% versus 5% for the uncatalyzed reaction. An ee of 12% was observed for the major diastereomer When N-Boc alkyl imines were employed under the same reaction conditions a significant drop in ee was observed. In the case of the cyclohexanecarboxaldehyde derived imine the desired product was isolated in 60% yield with a 26% ee
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2) = 0.110 [I > 2σ(I)]. The structure was solved with SHELXS-97, and refined with SHELXL-97. CCDC reference number 626419. For crystallographic data in CIF or other electronic format see DOI:
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