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

doi:10.6023/cjoc202405039

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3739-3746.DOI: 10.6023/cjoc202405039 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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References 12

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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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