PIII-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins

doi:10.6023/cjoc202104036

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4066-4074.DOI: 10.6023/cjoc202104036 Previous Articles Next Articles

Special Issue: 南开大学化学学科创立100周年

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三价磷介导的分子内环丙烷化反应及环丙烷并[c]香豆素的合成

仇裕鹤^a, 鲁康辉^a, 韦邦尺^a, 潜振凯^a, 贺峥杰^a^,^b^,^*()

a 南开大学化学学院元素有机化学国家重点实验室天津 300071
b 天津化学化工协同创新中心天津 300071

收稿日期:2021-04-17 修回日期:2021-05-07 发布日期:2021-06-02
通讯作者: 贺峥杰
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21472096); 国家自然科学基金(J1103308)

P^III-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins

Yuhe Qiu^a, Kanghui Lu^a, Bangchi Wei^a, Zhenkai Qian^a, Zhengjie He^a^,^b()

a State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071

Received:2021-04-17 Revised:2021-05-07 Published:2021-06-02
Contact: Zhengjie He
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21472096); National Natural Science Foundation of China(J1103308)

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Abstract

Under the treatment of P(NMe₂)₃, benzoylformates bearing an α,β-unsaturated ketone unit readily underwent an intramolecular cyclopropanation reaction, producing the corresponding cyclopropa[c]coumarins in moderate to good yields. Under the optimized conditions, the reaction exhibited a wide scope of substrates and excellent stereoselectivity, thus provides a facile and efﬁcient method for the synthesis of cyclopropa[c]coumarins.

Key words: benzoylformates, cyclopropanation reaction, cyclopropa[c]coumarins, phosphorus reagent

Cite this article

Yuhe Qiu, Kanghui Lu, Bangchi Wei, Zhenkai Qian, Zhengjie He. P^III-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4066-4074.

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Entry	PR₃	Solvent	Time/h	Yield^b/%	dr^d
1	P(NMe₂)₃	CH₂Cl₂	4	45	>20∶1
2	PPh₃	CH₂Cl₂	4	NR^c	—
3	P(OMe)₃	CH₂Cl₂	4	35	>20∶1
4	PBu₃	CH₂Cl₂	4	15	>20∶1
5	P(NMe₂)₃	CHCl₃	4	40	>20∶1
6	P(NMe₂)₃	ClCH₂CH₂Cl	4	37	>20∶1
7	P(NMe₂)₃	THF	4	35	>20∶1
8	P(NMe₂)₃	Toluene	4	65	>20∶1
9	P(NMe₂)₃	Toluene	2	48	>20∶1
10	P(NMe₂)₃	Toluene	6	71	>20∶1
11	P(NMe₂)₃	Toluene	8	70	>20∶1
12	P(NMe₂)₃	Toluene	10	71	>20∶1

Entry	PR₃	Solvent	Time/h	Yield^b/%	dr^d
1	P(NMe₂)₃	CH₂Cl₂	4	45	>20∶1
2	PPh₃	CH₂Cl₂	4	NR^c	—
3	P(OMe)₃	CH₂Cl₂	4	35	>20∶1
4	PBu₃	CH₂Cl₂	4	15	>20∶1
5	P(NMe₂)₃	CHCl₃	4	40	>20∶1
6	P(NMe₂)₃	ClCH₂CH₂Cl	4	37	>20∶1
7	P(NMe₂)₃	THF	4	35	>20∶1
8	P(NMe₂)₃	Toluene	4	65	>20∶1
9	P(NMe₂)₃	Toluene	2	48	>20∶1
10	P(NMe₂)₃	Toluene	6	71	>20∶1
11	P(NMe₂)₃	Toluene	8	70	>20∶1
12	P(NMe₂)₃	Toluene	10	71	>20∶1

三价磷介导的分子内环丙烷化反应及环丙烷并[c]香豆素的合成

P^III-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins

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