Chiral phosphoric acid catalyzed enantioselective inverse-electron-demand oxa-Diels–Alder reactions to synthesize chiral tricyclic tetrahydropyran derivatives
文献信息
发布日期
2023-11-23
DOI
10.1039/D3QO01615C
影响因子
5.281
作者
Fang Tian, Lin Peng, Liang-Liang Wang
查看原文
摘要
A series of enantioenriched tricyclic tetrahydropyran derivatives were achieved through chiral phosphoric acid catalyzed intramolecular inverse electron demand oxa-Diels–Alder (IEDODA) reactions, with good yields (up to 95%) and excellent stereocontrol (>20 : 1 dr, up to 99% ee). The achievement of such high enantioselectivity was ascribed to the rationally designed remote dual hydrogen bonding interaction, by which the conformation of the flexible substrate was well arranged by the catalyst in a reactive and stereoselective manner to participate in the transformation.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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