Pd-Catalyzed Enantio- and Diastereo-selective Hydrocarboxylation of Trisubstituted Alkenes

doi:10.6023/cjoc202402003

Abstract

A palladium-catalyzed asymmetric intermolecular hydrocarboxylation of trisubstituted alkenes was reported, which afforded a series of succinic acid derivatives containing two chiral centers with moderate to excellent yields, enantioselectivity, and high diastereoselectivity. The resulting dimethyl succinates can be easily converted to optically active γ-butyrolactones, demonstrating the potential application of this method.

Key words: palladium, asymmetric, hydrocarbonylation, alkene, succinic acid, carbon monoxide

Cite this article

Zhen Wang, Kaiwu Dong. Pd-Catalyzed Enantio- and Diastereo-selective Hydrocarboxylation of Trisubstituted Alkenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3249-3257.

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Entry	X	[Pd]	L	Solvent	2a^h
Entry	X	[Pd]	L	Solvent	Yield/ %	ee/%			dr
1	OMe	Pd(OAc)₂	L1	MeOH	18		69	>20:1
2	OMe	Pd(acac)₂	L1	MeOH	22		63	11:1
3	OMe	Pd(CH₂CN)Cl₂	L1	MeOH	19		66	10:1
4	OMe	Pd(PPh₃)Cl₂	L1	MeOH	23		68	10:1
5	OMe	Pd(dppf)Cl₂	L1	MeOH	26		7	9:1
6	OMe	Pd(dba)₂	L1	MeOH
7	OMe	Pd₂(dba)₃	L1	MeOH
8	OMe	PdCl₂	L1	MeOH	9		65	9:1
9	OMe	PdBr₂	L1	MeOH	6		69	11:1
10	OMe	Pd(OAc)₂	L2	MeOH	17		59	>20:1
11	OMe	Pd(OAc)₂	L3	MeOH	42		3	2:1
12	OMe	Pd(OAc)₂	L4	MeOH	16		12	9:1
13	OMe	Pd(OAc)₂	L5	MeOH	32		7	13:1
14	OMe	Pd(OAc)₂	L6	MeOH	36		4	16:1
15	OMe	Pd(OAc)₂	L7	MeOH	28		79	11:1
16	OMe	Pd(OAc)₂	L8	MeOH	32		85	>20:1
17	OMe	Pd(OAc)₂	L9	MeOH	20		86	>20:1
18^b	OMe	Pd(OAc)₂	L8	Toluene	36		87	>20:1
19^b	OMe	Pd(OAc)₂	L8	THF	16		85	>20:1
20^b	OMe	Pd(OAc)₂	L8	1,4-Dioxane	17		87	>20:1
21^b	OMe	Pd(OAc)₂	L8	n-Hexane	35		86	>20:1
22^b	OMe	Pd(OAc)₂	L8	Xylene	34		87	>20:1
23^b^,^c	OMe	Pd(OAc)₂	L8	Toluene	42		89	>20:1
24^d	OMe	Pd(OAc)₂	L8	Toluene	43		89	>20:1
25	OH	Pd(OAc)₂	L8	MeOH	42		89	>20:1
26^d	OH	Pd(OAc)₂	L8	Toluene	51		92	>20:1
27^d,e	OH	Pd(OAc)₂	L8	Toluene	73 (70ⁱ)		92	>20:1
28^d^,^f	OH	Pd(OAc)₂	L8	Toluene	32		92	>20:1
29^d^,^g	OH	Pd(OAc)₂	L8	Toluene	<10		93	>20:1

Entry	X	[Pd]	L	Solvent	2a^h
Entry	X	[Pd]	L	Solvent	Yield/ %	ee/%			dr
1	OMe	Pd(OAc)₂	L1	MeOH	18		69	>20:1
2	OMe	Pd(acac)₂	L1	MeOH	22		63	11:1
3	OMe	Pd(CH₂CN)Cl₂	L1	MeOH	19		66	10:1
4	OMe	Pd(PPh₃)Cl₂	L1	MeOH	23		68	10:1
5	OMe	Pd(dppf)Cl₂	L1	MeOH	26		7	9:1
6	OMe	Pd(dba)₂	L1	MeOH
7	OMe	Pd₂(dba)₃	L1	MeOH
8	OMe	PdCl₂	L1	MeOH	9		65	9:1
9	OMe	PdBr₂	L1	MeOH	6		69	11:1
10	OMe	Pd(OAc)₂	L2	MeOH	17		59	>20:1
11	OMe	Pd(OAc)₂	L3	MeOH	42		3	2:1
12	OMe	Pd(OAc)₂	L4	MeOH	16		12	9:1
13	OMe	Pd(OAc)₂	L5	MeOH	32		7	13:1
14	OMe	Pd(OAc)₂	L6	MeOH	36		4	16:1
15	OMe	Pd(OAc)₂	L7	MeOH	28		79	11:1
16	OMe	Pd(OAc)₂	L8	MeOH	32		85	>20:1
17	OMe	Pd(OAc)₂	L9	MeOH	20		86	>20:1
18^b	OMe	Pd(OAc)₂	L8	Toluene	36		87	>20:1
19^b	OMe	Pd(OAc)₂	L8	THF	16		85	>20:1
20^b	OMe	Pd(OAc)₂	L8	1,4-Dioxane	17		87	>20:1
21^b	OMe	Pd(OAc)₂	L8	n-Hexane	35		86	>20:1
22^b	OMe	Pd(OAc)₂	L8	Xylene	34		87	>20:1
23^b^,^c	OMe	Pd(OAc)₂	L8	Toluene	42		89	>20:1
24^d	OMe	Pd(OAc)₂	L8	Toluene	43		89	>20:1
25	OH	Pd(OAc)₂	L8	MeOH	42		89	>20:1
26^d	OH	Pd(OAc)₂	L8	Toluene	51		92	>20:1
27^d,e	OH	Pd(OAc)₂	L8	Toluene	73 (70ⁱ)		92	>20:1
28^d^,^f	OH	Pd(OAc)₂	L8	Toluene	32		92	>20:1
29^d^,^g	OH	Pd(OAc)₂	L8	Toluene	<10		93	>20:1

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