Enantioselective Organocatalytic Synthesis of δ-Lactone-Fused 4-Chromanones

Yu Ting Lai, Koppanathi Nagaraju, Ramani Gurubrahamam, Kwunmin Chen*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

4 引文 斯高帕斯(Scopus)

摘要

An organocatalytic enantioselective synthesis of δ-lactone-fused 4-chromanones was demonstrated using 1-(2-hydroxyaryl)-1,3-butanedione and α,β-unsaturated aldehydes in the presence of the Jørgensen-Hayashi catalyst. The reaction proceeded through a Michael addition/cycloketalization/hemiacetalization sequence, and the resulting hemiacetals were oxidized into the corresponding lactone derivatives in a one-pot manner. The desired fused O,O-ketal tricyclic lactone motifs containing three contiguous chiral centers were obtained in excellent chemical yields (up to 97%) and with high stereoselectivities (up to >20:1 dr and up to 95% ee). (Figure presented.).

原文英語
頁(從 - 到)3846-3850
頁數5
期刊Advanced Synthesis and Catalysis
362
發行號18
DOIs
出版狀態已發佈 - 2020 9月 21

ASJC Scopus subject areas

  • 催化
  • 有機化學

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