Chiral Metal Salts as Ligands for Catalytic Asymmetric Mannich Reactions with Simple Amides

Yasuhiro Yamashita, Aika Noguchi, Seiya Fushimi, Miho Hatanaka, Shū Kobayashi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5598-5604
Number of pages7
JournalJournal of the American Chemical Society
Volume143
Issue number15
DOIs
Publication statusPublished - 2021 Apr 21

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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