Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence

doi:10.6023/cjoc202211035

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2120-2125.DOI: 10.6023/cjoc202211035 Previous Articles Next Articles

借助有机催化去共轭-羟醛缩合反应来获得α-乙烯基-β-炔基取代的烯醛

全翌雯^a, 蒋心惠^b^,^*(), 李文军^c, 汪舰^c^,^*()

a 重庆医科大学第一临床医学院重庆 400016
b 重庆医科大学药学院重庆 400016
c 清华大学药学院北京 100084

收稿日期:2022-11-28 修回日期:2022-12-24 发布日期:2023-01-11
基金资助:
国家自然科学基金(21871160); 国家自然科学基金(21672121); 国家自然科学基金(22071130)

Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence

Yiwen Quan^a, Xinhui Jiang^b,*(), Wenjun Li^c, Jian Wang^c,*()

a The First College of Clinical Medicine, Chongqing Medical University, Chongqing 400016
b School of Pharmacy, Chongqing Medical University, Chongqing 400016
c School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084

Received:2022-11-28 Revised:2022-12-24 Published:2023-01-11
Contact: * E-mail: jiangxinhui@cqmu.edu.cn;wangjian2012@tsinghua.edu.cn
Supported by:
National Natural Science Foundation of China(21871160); National Natural Science Foundation of China(21672121); National Natural Science Foundation of China(22071130)

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Yiwen Quan, Xinhui Jiang, Wenjun Li, Jian Wang. Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2120-2125.

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References 17

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Entry	Cat.	Solvent	Base	Yield^b/%
1	I	CH₂Cl₂	K₂CO₃	<5
2	II	CH₂Cl₂	K₂CO₃	55
3	III	CH₂Cl₂	K₂CO₃	58
4	IV	CH₂Cl₂	K₂CO₃	16
5	V	CH₂Cl₂	K₂CO₃	65
6	V	CH₂Cl₂	—	13
7	V	CH₂Cl₂	Cs₂CO₃	63
8	V	CH₂Cl₂	Na₂CO₃	37
9	V	CH₂Cl₂	NaOAc	32
10	V	CH₂Cl₂	Et₃N	56
11	V	CH₂Cl₂	DBU	54
12	V	CH₂Cl₂	AcOH	14
13	V	CHCl₃	K₂CO₃	73
14	V	THF	K₂CO₃	52
15	V	Toluene	K₂CO₃	87
16	V	DMSO	K₂CO₃	<5
17^c	V	Toluene	K₂CO₃	78

Entry	Cat.	Solvent	Base	Yield^b/%
1	I	CH₂Cl₂	K₂CO₃	<5
2	II	CH₂Cl₂	K₂CO₃	55
3	III	CH₂Cl₂	K₂CO₃	58
4	IV	CH₂Cl₂	K₂CO₃	16
5	V	CH₂Cl₂	K₂CO₃	65
6	V	CH₂Cl₂	—	13
7	V	CH₂Cl₂	Cs₂CO₃	63
8	V	CH₂Cl₂	Na₂CO₃	37
9	V	CH₂Cl₂	NaOAc	32
10	V	CH₂Cl₂	Et₃N	56
11	V	CH₂Cl₂	DBU	54
12	V	CH₂Cl₂	AcOH	14
13	V	CHCl₃	K₂CO₃	73
14	V	THF	K₂CO₃	52
15	V	Toluene	K₂CO₃	87
16	V	DMSO	K₂CO₃	<5
17^c	V	Toluene	K₂CO₃	78

借助有机催化去共轭-羟醛缩合反应来获得α-乙烯基-β-炔基取代的烯醛

Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence

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