Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates

doi:10.6023/cjoc202010040

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1614-1621.DOI: 10.6023/cjoc202010040 Previous Articles Next Articles

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三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应

马海^a, 于广浩^a, 隋峰^a, 杨米一^a, 刘丽^a, 李慧杰^a, 李峰^b^,^*(), 赵庆贺^a^,^*()

a 中国中医科学院中药研究所北京 100700
b 商丘师范学院化学化工学院药物绿色合成河南省工程实验室河南商丘 476000

收稿日期:2020-10-29 修回日期:2020-12-05 发布日期:2020-12-24
通讯作者: 李峰, 赵庆贺
作者简介:
† 共同第一作者(These authors contributed equally to this work).
基金资助:
中国中医科学院自主研发(ZZ0908028)

Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates

Hai Ma^a, Guanghao Yu^a, Feng Sui^a, Miyi Yang^a, Li Liu^a, Huijie Li^a, Feng Li^b^,^*(), Qinghe Zhao^a^,^*()

a Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700
b College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000

Received:2020-10-29 Revised:2020-12-05 Published:2020-12-24
Contact: Feng Li, Qinghe Zhao
About author:
* Corresponding authors. E-mail: qhzhao@icmm.ac.cn;
E-mail: lifeng20150720@163.com
Supported by:
Voluntary Program of China Academy of Chinese Medical Sciences(ZZ0908028)

1. cjoc202010040辅助材料.pdf(2315KB)

Abstract

Et₃N-catalyzed cascade reaction of trifluoromethyl ketones and γ-hydroxy-α,β-unsaturated ketones via hemiketal intermediate is investigated. The adducts could be easily obtained in good to excellent yields with moderate diastereoselectivities. The reaction proceeded smoothly to give the desired product in 92% yield and with 96% ee in the presence of a glycosyl and quinidine-based bifunctional chiral thiourea catalyst.

Key words: γ-hydroxy-α,β-unsaturated ketone, trifluoromethyl ketone, 1,3-dioxolanes derivative, chiral thiourea

Cite this article

Hai Ma, Guanghao Yu, Feng Sui, Miyi Yang, Li Liu, Huijie Li, Feng Li, Qinghe Zhao. Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1614-1621.

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References 11

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Entry	Catalyst	Solvent	T/℃	Yield^b/%	dr^c
1	E₃N	Et₂O	25	95	60∶40
2	DABCO	Et₂O	25	85	65∶35
3	DBU	Et₂O	25	82	65∶35
4	Ph₃P	Et₂O	25	—	—
5	DMAP	Et₂O	25	70	55∶45
6	Na₂CO₃	Et₂O	25	42	55∶45
7	K₂CO₃	Et₂O	25	40	55∶45
8	Et₃N	CH₂Cl₂	25	90	50∶50
9	Et₃N	PhMe	25	85	55∶45
10	Et₃N	THF	25	92	60∶40
11	Et₃N	MTBE	25	99	70∶30

Entry	Catalyst	Solvent	T/℃	Yield^b/%	dr^c
1	E₃N	Et₂O	25	95	60∶40
2	DABCO	Et₂O	25	85	65∶35
3	DBU	Et₂O	25	82	65∶35
4	Ph₃P	Et₂O	25	—	—
5	DMAP	Et₂O	25	70	55∶45
6	Na₂CO₃	Et₂O	25	42	55∶45
7	K₂CO₃	Et₂O	25	40	55∶45
8	Et₃N	CH₂Cl₂	25	90	50∶50
9	Et₃N	PhMe	25	85	55∶45
10	Et₃N	THF	25	92	60∶40
11	Et₃N	MTBE	25	99	70∶30

三乙胺催化的γ-羟基-α,β-不饱和酮与三氟甲基酮通过半缩酮中间体的级联反应

Triethylamine-Catalyzed Cascade Reaction of γ-Hydroxy-α,β-unsaturated Ketones with Trifluoromethyl Ketones via Hemiketal Intermediates

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