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Proline‐Catalyzed Mannich Reaction of Aldehydes with N‐Boc‐Imines

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Yang,  Jung Woon
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Stadler,  Michael
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

Yang, J. W., Stadler, M., & List, B. (2007). Proline‐Catalyzed Mannich Reaction of Aldehydes with N‐Boc‐Imines. Angewandte Chemie International Edition, 46(4), 609-611. doi:10.1002/anie.200603188.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A45C-C
Abstract
A curious cat.: The proline‐catalyzed Mannich reaction between aldehydes and N‐Boc‐imines (Boc=tert‐butoxycarbonyl) gives crystalline β‐amino aldehydes with exceptionally high diastereoselectivities and enantioselectivities (see scheme). The products of this reaction typically precipitate from the reaction mixture and are useful intermediates in the synthesis of α‐ and β‐substituted β‐amino acids.