Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1399-1406.DOI: 10.6023/cjoc201402028 Previous Articles     Next Articles

ARTICLE

乙醛和不饱和三氟甲基酮不对称Aldol反应合成光学活性的β-三氟甲基-β-羟基-δ-戊内酯

姚子丽, 康泰然, 何龙, 刘全忠   

  1. 化学合成与污染控制四川省重点实验室 西华师范大学化学化工学院 南充 637009
  • 收稿日期:2014-02-24 修回日期:2014-03-17 发布日期:2014-04-01
  • 通讯作者: 刘全忠 E-mail:quanzhongliu@cwnu.edu.cn
  • 基金资助:

    四川省省属高校科研创新团队基金(No.14TD0016)资助项目.

Synthesis of Optically Enriched β-Trifloromethyl-δ-lactones through Asymmetric Aldol Reactions of Acetaldehyde with Unsaturated Trifluoromethyl Ketones as the Key Steps

Yao Zili, Kang Tairan, He Long, Liu Quanzhong   

  1. Key Laboratory of Chemical Synthesis and Pollution Control of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637009
  • Received:2014-02-24 Revised:2014-03-17 Published:2014-04-01
  • Supported by:

    Project supported by the Innovative Research Team in College of Sichuan Province (No. 14TD0016).

Optically enriched δ-lactones with a quaternary trifluoromethyl carbinol motif were synthesized in good yields with high to excellent enantioselectivities. The synthesis step includes asymmetric aldol reactions of acetaldehyde with unsaturated trifluoromethyl ketones followed by oxidations and a subsequent iodolactonization and deiodination.

Key words: δ-lactones, aldol reactions, iodolactonization, deiodination