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.
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Acknowledgements
Generous support by the Max-Planck-Society, the Fonds der Chemischen Industrie (Silver Award to B.L.), and by Novartis (Young Investigator Award to B.L.) is gratefully acknowledged. We also thank Merck, Saltigo, and Wacker for support, and BASF and Degussa for donating chemicals.
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Yang, J., Stadler, M. & List, B. Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. Nat Protoc 2, 1937–1942 (2007). https://doi.org/10.1038/nprot.2007.272
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DOI: https://doi.org/10.1038/nprot.2007.272
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