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Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids

MPS-Authors
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Zhu,  Chendan
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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

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Maji,  Rajat
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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jacs.1c00249.pdf
(Postprint), 2MB

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Citation

Zhu, C., Mandrelli, F., Zhou, H., Maji, R., & List, B. (2021). Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids. Journal of the American Chemical Society, 143(9), 3312-3317. doi:10.1021/jacs.1c00249.


Cite as: http://hdl.handle.net/21.11116/0000-0008-315F-7
Abstract
We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.