Enantioselective aza-Friedel-Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts

Manabu Hatano, Haruka Okamoto, Taro Kawakami, Kohei Toh, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Chiral C2- and C1-symmetric BINOL-derived bis(phosphoric acid) catalysts, which have OP(=O)(OH)2/OP(=O)(OH)(OR) moieties at the 2,2′-positions, were developed and used for the enantioselective aza-Friedel-Crafts reaction of 2-methoxyfuran with α-ketimino esters for the first time. The intramolecular conjugated double hydrogen bond network is a key to increasing the Brønsted acidity and preventing deactivation of the catalysts. Highly functionalized α-amino acid derivatives with a chiral quaternary carbon center could be transformed into versatile optically active N- and O-heterocycles and an α-aryl-substituted serine.

Original languageEnglish
Pages (from-to)6361-6367
Number of pages7
JournalChemical Science
Volume9
Issue number30
DOIs
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Chemistry(all)

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