N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones

doi:10.6023/cjoc202105002

Abstract

Asymmetric synthesis of chiral organosilanes with a potential application was realized by N-heterocyclic carbene- catalyzed [4+2] annulation of acetates and β-silyl enones. This strategy exhibits easy to obtain raw materials, mild reaction conditions, good substrate tolerance, simple operation and so on. Notably, excellent yield and enantioselectivity were also observed with expanding the reaction scale by 10 times. The target product showed excellent results in hydrogenation reduction. Moreover, the hypolipidemic drug ezetimibe was obtained through the synthetic transformation of the resulting products.

Key words: N-heterocyclic carbene, chiral organosilanes, asymmetric catalysis, β-silyl enone, acetate

Cite this article

Yuxia Zhang, Jingcheng Guo, Jie Huang, Zhenqian Fu. N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4467-4475.

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Entry	NHC	1	Base	Solvent	Yield^b/%	ee^c/%
1	A	1a	DBU	THF	44	—
2	B	1a	DBU	THF	17	99
3	B	1b	DBU	THF	88	99
3	B	1b	DBU	1,4-Dioxane	55	99
4	B	1b	DBU	CH₃CN	54	99
5	B	1b	DBU	TOL	66	99
6	B	1b	DBU	DCM	66	99
7	B	1b	DBU	CHCl₃	57	99
8	B	1b	Et₃N	THF	50	99
9	B	1b	DIPEA	THF	49	99
10	B	1b	K₂CO₃	THF	40	99
11	B	1b	DMAP	THF	51	99
12	B	1b	DBN	THF	85	99
13^d	B	1b	DBU	THF	86	99
14^e	B	1b	DBU	THF	74	99
15^f	B	1b	DBU	THF	69	99
16^d^,^g	B	1b	DBU	THF	80	99

Entry	NHC	1	Base	Solvent	Yield^b/%	ee^c/%
1	A	1a	DBU	THF	44	—
2	B	1a	DBU	THF	17	99
3	B	1b	DBU	THF	88	99
3	B	1b	DBU	1,4-Dioxane	55	99
4	B	1b	DBU	CH₃CN	54	99
5	B	1b	DBU	TOL	66	99
6	B	1b	DBU	DCM	66	99
7	B	1b	DBU	CHCl₃	57	99
8	B	1b	Et₃N	THF	50	99
9	B	1b	DIPEA	THF	49	99
10	B	1b	K₂CO₃	THF	40	99
11	B	1b	DMAP	THF	51	99
12	B	1b	DBN	THF	85	99
13^d	B	1b	DBU	THF	86	99
14^e	B	1b	DBU	THF	74	99
15^f	B	1b	DBU	THF	69	99
16^d^,^g	B	1b	DBU	THF	80	99

氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯