An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition

Chi Han Chen, Chi Ting Ko, Ganapuram Madhusudhan Reddy, Chia Jui Lee, Wenwei Lin*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

9 引文 斯高帕斯(Scopus)

摘要

A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.

原文英語
頁(從 - 到)5254-5265
頁數12
期刊European Journal of Organic Chemistry
2015
發行號23
DOIs
出版狀態已發佈 - 2015 八月 1

ASJC Scopus subject areas

  • 物理與理論化學
  • 有機化學

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