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  Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids

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.

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 Creators:
Zhu, Chendan1, Author              
Mandrelli, Francesca1, Author              
Zhou, Hui1, Author              
Maji, Rajat1, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 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.

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Language(s): eng - English
 Dates: 2021-01-082021-03-012021-03-10
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.1c00249
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 143 (9) Sequence Number: - Start / End Page: 3312 - 3317 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870