TY - JOUR
T1 - Chiral Metal Salts as Ligands for Catalytic Asymmetric Mannich Reactions with Simple Amides
AU - Yamashita, Yasuhiro
AU - Noguchi, Aika
AU - Fushimi, Seiya
AU - Hatanaka, Miho
AU - Kobayashi, Shū
N1 - Funding Information:
This work was partially supported by the Agency for Medical Research and Development (S.K.), and the Japan Society for the Promotion of Science KAKENHI Grant Numbers JP 17H06448 (Y.Y.) and JP 17H06445 (M.H.). S.F. is grateful for the financial support provided by the Japan Chemical Industry Association. The authors thank Dr. Ramamurthy Nagarajaprakash and Dr. Zhonghua Xia for their technical assistance for this work.
Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/4/21
Y1 - 2021/4/21
N2 - Catalytic asymmetric Mannich reactions of imines with weakly acidic simple amides were developed using a chiral potassium hexamethyldisilazide (KHMDS)-bis(oxazoline) potassium salt (K-Box) catalyst system. The desired reactions proceeded to afford the target compounds in high yields with high diastereo- and enantioselectivities. It was suggested that a K enolate interacted with K-Box to form a chiral K enolate that reacted with imines efficiently. In this system, K-Box (potassium salt of Box) worked as a chiral ligand of the active potassium species.
AB - Catalytic asymmetric Mannich reactions of imines with weakly acidic simple amides were developed using a chiral potassium hexamethyldisilazide (KHMDS)-bis(oxazoline) potassium salt (K-Box) catalyst system. The desired reactions proceeded to afford the target compounds in high yields with high diastereo- and enantioselectivities. It was suggested that a K enolate interacted with K-Box to form a chiral K enolate that reacted with imines efficiently. In this system, K-Box (potassium salt of Box) worked as a chiral ligand of the active potassium species.
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U2 - 10.1021/jacs.0c13317
DO - 10.1021/jacs.0c13317
M3 - Article
C2 - 33821631
AN - SCOPUS:85105072193
SN - 0002-7863
VL - 143
SP - 5598
EP - 5604
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 15
ER -