Brønsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Norie Momiyama, Hisashi Yamamoto

研究成果: Article査読

257 被引用数 (Scopus)

抄録

Two types of chiral Brønsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Brønsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Brønsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Brønsted acidity.

本文言語English
ページ(範囲)1080-1081
ページ数2
ジャーナルJournal of the American Chemical Society
127
4
DOI
出版ステータスPublished - 2005 2月 2
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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