Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities

Azusa Kondoh, Masafumi Oishi, Hikaru Tezuka, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

In the field of chiral Brønsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Brønsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich-type reaction of α-phenylthioacetate as a less acidic pronucleophile. The present achievement would provide a new guiding principle for the design and development of chiral Brønsted base catalysts and significantly broaden the utility of Brønsted base catalysis in asymmetric organic synthesis.

Original languageEnglish
Pages (from-to)7472-7477
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number19
DOIs
Publication statusPublished - 2020 May 4

Keywords

  • asymmetric catalysis
  • guanidine
  • organocatalyst
  • organosuperbase
  • phosphazene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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