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The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines

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Chandler,  Carley
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Galzerano,  Patrizia
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Michrowska,  Anna
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Chandler, C., Galzerano, P., Michrowska, A., & List, B. (2009). The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines. Angewandte Chemie International Edition, 48(11), 1978-1980. doi:10.1002/anie.200806049.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-8F5B-6
Abstract
Double‐cross: Proline catalyzes the double Mannich reaction of acetaldehyde with N‐Boc imines in excellent yields (up to 99 %; Boc=tert‐butoxycarbonyl) and close to perfect diastereo‐ and enantioselectivities. Depending on the choice of catalysts, both the chiral, pseudo‐C2‐symmetric diastereomer and the corresponding meso compound can be prepared. Cross double Mannich reactions of acetaldehyde with two different imines are also demonstrated.