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

Chandler, Carley; Galzerano, Patrizia; Michrowska, Anna; List, Benjamin

doi:10.1002/anie.200806049

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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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引用

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.

引用: https://hdl.handle.net/11858/00-001M-0000-000F-8F5B-6

要旨

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.