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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References 12

[1]	(a) Harrington, P. J.; Lodewijk, E. Org. Process Res. Dev. 1997, 1, 72. pmid: 31471864
	(b) Magnus, N. A.; Braden, T. M.; Buser, J. Y.; DeBaillie, A. C.; Heath, P. C.; Ley, C. P.; Remacle, J. R.; Varie, D. L.; Willson, T. M. Org. Process Res. Dev. 2012, 16, 830. pmid: 31471864
	(c) DeBaillie, A. C.; Magnus, N. A.; Laurila, M. E.; Wepsiec, J. P.; Ruble, J. C.; Petkus, J. J.; Vaid, R. K.; Niemeier, J. K.; Mick, J. F.; Gunter, T. Z. Org. Process Res. Dev. 2012, 16, 1538. pmid: 31471864
	(d) Yamagami, T.; Moriyama, N.; Kyuhara, M.; Moroda, A.; Uemura, T.; Matsumae, H.; Moritani, Y.; Inoue, I. Org. Process Res. Dev. 2014, 18, 437. pmid: 31471864
	(e) Wang, J.; Xu, C.; Wong, Y.; Li, Y.; Liao, F.; Jiang, T.; Tu, Y. Engineering 2019, 5, 32. pmid: 31471864
	(f) Deeks, E. D. Clin. Drug Invest. 2019, 39, 1133. doi: 10.1007/s40261-019-00843-z pmid: 31471864
	(g) Ma, K. Q.; Martin, B. S.; Yin, X.; Dai, M. Nat. Prod. Rep. 2019, 36, 174. pmid: 31471864
[2]	(a) Consiglio, G. Helv. Chim. Acta 1976, 59, 124.
	(b) Hayashi, T.; Tanaka, M.; Ogata, I. Tetrahedron Lett. 1978, 41, 3925.
	(c) Cometti, G.; Chiusoli, G. P. J. Org. Chem. 1982, 236, C31.
	(d) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Marchetti, M. Tetrahedron: Asymmetry 1994, 5, 299.
	(e) Yu, W.-Y.; Bensimon, C.; Alper, H. Chem.-Eur. J. 1997, 3, 417.
	(f) Godard, C.; Muñoz, B. K.; Ruiz, A.; Claver, C. Dalton Trans. 2008, 853.
	(g) Kalck, P.; Urrutigoity, M. Inorg. Chim. Acta 2015, 431, 110.
[3]	(a) Franke, R.; Selent, D.; Börner, A. Chem. Rev. 2012, 112, 5675. pmid: 31857484
	(b) Dong, K.; Fang, X. Gülak, S.; Franke, R.; Spannenberg, A.; Neumann, H.; Jackstell, R.; Beller, M. Nat. Commun. 2017, 8, 14117. pmid: 31857484
	(c) Yang, J.; Liu, J.; Neumann, H.; Franke, R.; Jackstell, R.; Beller, M. Science 2019, 366, 1514. doi: 10.1126/science.aaz1293 pmid: 31857484
	(d) Yang, J.; Liu, J.; Ge, Y.; Huang, W.; Ferretti, F.; Neumann, H.; Jiao, H.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem. Int. Ed. 2021, 133, 9613. pmid: 31857484
	(e) Yang, J.; Wang, P.; Neumann, H.; Jackstell, R.; Beller, M. Ind. Chem. Mater. 2023, 1, 155. pmid: 31857484
[4]	(a) Li, J.; Shi, Y. Chem. Soc. Rev. 2022, 51, 6757.
	(b) Shen, C.; Dong, K. Synlett 2022, 33, 815.
	(c) Peng, J. -B.; Liu, X. -L.; Li, L.; Wu, X. Sci. China Chem. 2022, 65,441.
	(d) Yu, R.; Cai, S. -Z.; Li, C.; Fang, X. Angew. Chem. Int. Ed. 2022, 134, e202200733.
	(e) Li, Q.; Zhang, Y.; Liu, P.; Zhong, J.; Gong, B.; Yao, H.; Lin, A. Angew. Chem. Int. Ed. 2023, 135, e202211988.
	(f) Yin, X.; Li, S.; Guo, K.; Song, L.; Wang, X. Eur. J. Org. Chem. 2023, 26, e202300783.
[5]	(a) Morello, G. R.; Zhong, H.; Chirik, P. J.; Hopmann, K. H. Chem. Sci. 2018, 9, 4977. doi: 10.1039/c8sc01315b pmid: 29938025
	(b) Zhou, Y.; Xu, X.; Sun, H.; Tao, G.; Chang, X. -Y.; Xing, X.; Chen, B.; Xu, C. Nat. Commun. 2021, 12, 1953. pmid: 29938025
	(c) Dannenberg, S. G.; Seth Jr, D. M.; Finfer, E. J.; Waterman, R. ACS Catal. 2022, 13, 550. pmid: 29938025
[6]	(a) Arnaud, R.; Vetere, V.; Barone, V. Chem. Phys. Lett. 1998, 293, 295.
	(b) Adam, W.; Krebs, O.; Orfanopoulos, M.; Stratakis, M. J. Org. Chem. 2002, 67, 8395.
[7]	(a) Shing, T. K. M.; Leung, G. Y. C.; Luk, T. J. Org. Chem. 2005, 70, 7279. pmid: 19552449
	(b) Hedberg, C.; Källström, K.; Brandt, P.; Hansen, L. K.; Andersson, P. G. J. Am. Chem. Soc. 2006, 128, 2995. pmid: 19552449
	(c) Tolstoy, P.; Engman, M.; Paptchikhine, A.; Bergquist, J.; Church, T. L.; Leung, A. W.-M.; Andersson, P. G. J. Am. Chem. Soc. 2009, 131, 8855. doi: 10.1021/ja9013375 pmid: 19552449
	(d) Lu, P.; Lu, Z. Synthesis 2023, 55, 1042. pmid: 19552449
[8]	(a) Kong, W.; Wang, Q.; Zhu, J. Angew. Chem. Int. Ed. 2016, 55, 9714. pmid: 28345175
	(b) Yang, B.; Qiu, Y.; Jiang, T.; Wulff, W. D.; Yin, X.; Zhu, C.; Bäckvall, J. -E. Angew. Chem. Int. Ed. 2017, 56, 4535. doi: 10.1002/anie.201612385 pmid: 28345175
	(c) Han, A.; Tao, Y.; Reisman, S. E. Nature 2019, 573, 563. pmid: 28345175
	(d) Chen, M.; Wang, X.; Yang, P.; Kou, X.; Ren, Z. -H.; Guan, Z.-H. Angew. Chem. Int. Ed. 2020, 59, 12199. pmid: 28345175
[9]	Cao, P.; Zhang, X. J. Am. Chem. Soc. 1999, 121, 7708.
[10]	Ren, X.; Wang, Z.; Shen, C.; Tian, X.; Tang, L.; Ji, X.; Dong, K. Angew. Chem. Int. Ed. 2021, 60, 17693.
[11]	(a) Ji, X.; Shen, C.; Tian, X.; Dong, K. Org. Lett. 2021, 23, 8645.
	(b) Shi, Z.; Shen, C.; Dong, K. Chem. Eur. J. 2021, 27, 18039.
	(c) Ji, X.; Shen, C.; Tian, X.; Zhang, H.; Ren, X., Dong, K. Angew. Chem. Int. Ed. 2022, 61, e202204156.
[12]	(a) Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007, 5, 31.
	(b) Wang, D.-S.; Chen, Q.-A.; Li, W.; Yu, C.-B.; Zhou, Y.-G.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 8909.

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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