Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation

Daisuke Uraguchi, Masahiro Terada

Research output: Contribution to journalArticle

1047 Citations (Scopus)

Abstract

It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines. The beneficial effects of the 3,3′-bisaryl substituents of the catalysts on the enantioselectivity are greatly appreciated, and thus 1d functions as an excellent catalyst. The Brønsted acid-catalyzed direct Mannich reactions presented herein provide an attractive way to construct β-aminoketones under extremely mild conditions. The stereochemical course of this reaction was established through the synthesis of Boc-(S)-phenylglycine methylester. The transformation thus demonstrated is applicable to a useful method for the synthesis of various phenylglycine derivatives.

Original languageEnglish
Pages (from-to)5356-5357
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number17
DOIs
Publication statusPublished - 2004 May 5

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation'. Together they form a unique fingerprint.

  • Cite this