Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α‑Tertiary Amino Ketones from Sulfonium Ylides

Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-amino ketones, which is particularly useful for the less accessible acyclic α-tertiary cases. By a protonation–amination sequence, our approach represents a rare asymmetric H–heteroatom bond insertion by α-carbonyl...

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Veröffentlicht in:Journal of the American Chemical Society 2020-08, Vol.142 (33), p.14384-14390
Hauptverfasser: Guo, Wengang, Luo, Yuzheng, Sung, Herman H.-Y, Williams, Ian D, Li, Pingfan, Sun, Jianwei
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container_end_page 14390
container_issue 33
container_start_page 14384
container_title Journal of the American Chemical Society
container_volume 142
creator Guo, Wengang
Luo, Yuzheng
Sung, Herman H.-Y
Williams, Ian D
Li, Pingfan
Sun, Jianwei
description Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-amino ketones, which is particularly useful for the less accessible acyclic α-tertiary cases. By a protonation–amination sequence, our approach represents a rare asymmetric H–heteroatom bond insertion by α-carbonyl sulfonium ylides, an attractive surrogate of diazocarbonyls. The mild intermolecular C–N bond formation was catalyzed by chiral phosphoric acids with excellent efficiency and enantioselectivity. The products are precursors to other important chiral amine derivatives, including drug molecules and chiral ligands. The enantioselectivity was controlled by dynamic kinetic resolution in the amination step, rather than the initial protonation. This process opens up a new platform for the development of other related insertion reactions.
doi_str_mv 10.1021/jacs.0c07210
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subjects Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
title Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α‑Tertiary Amino Ketones from Sulfonium Ylides
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