有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应

doi:10.6023/cjoc202405039

有机化学 ›› 2024, Vol. 44 ›› Issue (12): 3739-3746.DOI: 10.6023/cjoc202405039 上一篇下一篇

研究论文

有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应

任岳, 史望宇, 唐义, 郭红超^*()

中国农业大学化学系北京 100193

收稿日期:2024-05-27 修回日期:2024-07-23 发布日期:2024-08-23
基金资助:
国家自然科学基金(22071264)

Phosphine-Catalyzed [5＋1] Annulation of Morita-Baylis-Hillman Carbonates with 1,3-Dicarbonyl Compounds

Yue Ren, Wangyu Shi, Yi Tang, Hongchao Guo^*()

Department of Chemistry, China Agricultural University, Beijing 100193

Received:2024-05-27 Revised:2024-07-23 Published:2024-08-23
Contact: *E-mail:hchguo@cau.edu.cn
Supported by:
National Natural Science Foundation of China(22071264)

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摘要/Abstract

报道了有机膦催化的Morita-Baylis-Hillman (MBH)碳酸酯与1,3-二羰基化合物的[5＋1]环化反应, 以高产率和中等至优秀的非对映选择性得到一系列具有潜在生物活性的螺环己烯衍生物. 该环化反应是通过膦叶立德用双亲核试剂的连续1,6-共轭加成/亲核取代反应实现的.

关键词: 有机膦催化, Morita-Baylis-Hillman碳酸酯, 1,3-二羰基化合物, 双亲核试剂, 螺环己烯

Phosphine-catalyzed [5＋1] annulation reaction of Morita-Baylis-Hillman (MBH) carbonates with 1,3-dicarbonyl compounds has been developed, producing biologically interesting spirocyclohexene derivatives in high yields with moderate to excellent diastereoselectivities. The annulation was achieved through sequential 1,6-conjugate addition/nucleophilic substu- tion reaction of phosphine ylides with dinucleophiles.

Key words: phosphine catalysis, Morita-Baylis-Hillman carbonate, 1,3-dicarbonyl compound, dinucleophile, spirocyclo- hexene

引用此文

任岳, 史望宇, 唐义, 郭红超. 有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应[J]. 有机化学, 2024, 44(12): 3739-3746.

Yue Ren, Wangyu Shi, Yi Tang, Hongchao Guo. Phosphine-Catalyzed [5＋1] Annulation of Morita-Baylis-Hillman Carbonates with 1,3-Dicarbonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3739-3746.

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Entry	Catalyst	Solvent	t/h	Yield^b/%	dr^c
1	PPh₃	MeCN	24	Trace	—
2	PPh₂Me	MeCN	24	45	10∶1
3	PPhMe₂	MeCN	36	38	7∶1
4	BnPPh₂	MeCN	24	74	>20∶1
5	BnPPh₂	CH₂Cl₂	36	41	6∶1
6	BnPPh₂	THF	48	46	7∶1
7	BnPPh₂	EtOAc	24	57	5∶1
8	BnPPh₂	Toluene	24	60	6∶1
9^d^,^f	BnPPh₂	MeCN	48	83	>20∶1
10^e^,^f	BnPPh₂	MeCN	48	81	>20∶1
11^d^,^g	BnPPh₂	MeCN	24	84	8∶1

Entry	Catalyst	Solvent	t/h	Yield^b/%	dr^c
1	PPh₃	MeCN	24	Trace	—
2	PPh₂Me	MeCN	24	45	10∶1
3	PPhMe₂	MeCN	36	38	7∶1
4	BnPPh₂	MeCN	24	74	>20∶1
5	BnPPh₂	CH₂Cl₂	36	41	6∶1
6	BnPPh₂	THF	48	46	7∶1
7	BnPPh₂	EtOAc	24	57	5∶1
8	BnPPh₂	Toluene	24	60	6∶1
9^d^,^f	BnPPh₂	MeCN	48	83	>20∶1
10^e^,^f	BnPPh₂	MeCN	48	81	>20∶1
11^d^,^g	BnPPh₂	MeCN	24	84	8∶1

有机膦催化的Morita-Baylis-Hillman碳酸酯与1,3-二羰基化合物的[5＋1]环化反应

Phosphine-Catalyzed [5＋1] Annulation of Morita-Baylis-Hillman Carbonates with 1,3-Dicarbonyl Compounds

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