Amphiphilic immobilized diphenylprolinol alkyl ether catalyst on PS-PEG resin

Seitaro Koshino, Shusuke Hattori, Shota Hasegawa, Naoki Haraguchi, Takeshi Yamamoto, Michinori Suginome, Yasuhiro Uozumi, Yujiro Hayashi

Research output: Contribution to journalReview articlepeer-review

Abstract

Diphenylprolinol silyl ether is a widely used organocatalyst, and its immobilization on a solid support was investigated for the easy recycling and reuse of this catalyst. Because a silyl ether bond of the catalyst is weak, its alkyl ether was attached to polymers such as a polyquinoxaline-based polymer, a polystyrene polymer (PS) resin, and a polystyrenepoly(ethylene glycol) graft copolymer (PS-PEG) resin. Although a polymer-supported organocatalyst generally decreases its reactivity compared with the monomer catalyst, diphenylprolinol anthrylmethyl ether supported on PS-PEG was found to be a reactive organocatalyst; it catalyzed the Michael reaction of an aldehyde and a nitroalkene in water without an organic solvent being present, with excellent diastereo- and enantioselectivities.

Original languageEnglish
Pages (from-to)790-797
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume94
Issue number3
DOIs
Publication statusPublished - 2021

Keywords

  • Asymmetric reaction
  • Organocatalyst
  • Polymer-supported catalyst

ASJC Scopus subject areas

  • Chemistry(all)

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