Organocatalytic asymmetric synthesis of both cis- and trans-configured pyrano[2,3-b]chromenes via different dehydration pathways

Autor: Xue-Jiao Lv, Yan-Kai Liu, Wei-Wei Zhao, Sheng-Biao Wan, Ying-Han Chen
Rok vydání: 2019
Předmět:
Zdroj: Organic Chemistry Frontiers. 6:1972-1976
ISSN: 2052-4129
DOI: 10.1039/c9qo00366e
Popis: The [3 + 3]-cycloaddition reaction of chroman-2-ols with β,γ-unsaturated α-ketoesters via an enamine-catalyzed sequential process is reported. The protocol provides efficient access to polycyclic hemiketal-containing compounds, which could be converted into both enantiomers of cis- and trans-fused pyrano[2,3-b]chromene derivatives with excellent stereoselectivity by different dehydration reaction pathways. The catalytic system could be recycled on a larger scale eight times without significantly affecting the yield and stereoselectivity. The possibilities for further structural diversification are demonstrated by various transformations.
Databáze: OpenAIRE