Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a beta-Diketone with Chiral Phase-Transfer Catalysts

作者:Yamamoto Eiji; Gokuden Daichi; Nagai Ayano; Kamachi Takashi; Yoshizawa Kazunari; Hamasaki Akiyuki; Ishida Tamao; Tokunaga Makoto*
来源:Organic Letters, 2012, 14(24): 6178-6181.
DOI:10.1021/ol3027363

摘要

Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

  • 出版日期2012-12-21