Enantioselective Organocatalytic Construction of Spirochroman Derivatives

Keisuke Yoshida, Hiroki Inoue, Yurika Oji, Hina Suzuki, Ken Ichi Takao

Research output: Contribution to journalArticle

Abstract

Highly enantioselective organocatalytic construction of spirochromans containing a tetrasubstituted stereocenter was developed. Intramolecular oxy-Michael addition was catalyzed with a bifunctional cinchona alkaloid thiourea catalyst. A variety of spirochroman compounds containing a tetrasubstituted stereocenter were obtained with excellent enantioselectivities of up to 99% enantiomeric excess. The reaction was applied to the asymmetric formal synthesis of (-)-(R)-cordiachromene.

Original languageEnglish
Pages (from-to)10189-10197
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number15
DOIs
Publication statusPublished - 2020 Aug 7

ASJC Scopus subject areas

  • Organic Chemistry

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