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Practical Proline-catalyzed asymmetric 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). Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. Nature Protocols, 2(8), 1937-1942. doi:10.1038/nprot.2007.272.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-927F-C
Abstract
This protocol describes a procedure for the synthesis of α, β-branched-b-amino aldehydes via Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-tert–butoxycarbonyl-imines. The crystalline β-amino aldehydes are formed in good yields and extremely high levels of diastereo- and enantioselectivities without the need for chromatographic purification and are readily oxidized to the corresponding β-amino acids. The protocol can be completed in approximately 14 h on small scales or up to 30 h on larger scales.