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

doi:10.6023/cjoc201402028

有机化学 ›› 2014, Vol. 34 ›› Issue (7): 1399-1406.DOI: 10.6023/cjoc201402028 上一篇下一篇

研究论文

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

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

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).

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摘要/Abstract

以手性伯胺为催化剂催化共轭不饱和三氟甲基酮与乙醛的不对称反应为关键步骤，合成了光学活性的β-三氟甲基-β-羟基-δ-戊内酯. 合成过程中包含乙醛和共轭不饱和三氟甲基酮的不对称Aldol反应、氧化反应、碘内酯化以及脱碘反应.

关键词: δ-戊内酯, 不对称Aldol反应, 碘内酯化, 脱碘反应

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

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姚子丽, 康泰然, 何龙, 刘全忠. 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[J]. 有机化学, 2014, 34(7): 1399-1406.

Yao Zili, Kang Tairan, He Long, Liu Quanzhong. Synthesis of Optically Enriched β-Trifloromethyl-δ-lactones through Asymmetric Aldol Reactions of Acetaldehyde with Unsaturated Trifluoromethyl Ketones as the Key Steps[J]. Chin. J. Org. Chem., 2014, 34(7): 1399-1406.

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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

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

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