Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation

Daisuke Uraguchi, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

1307 Citations (Scopus)


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
Issue number17
Publication statusPublished - 2004 May 5


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