Brønsted Acid-Catalyzed the Synthesis of Sulfoximide Substituted Dihydropyranone Derivatives

doi:10.6023/cjoc202108015

Abstract

Both sulfoximide and dihydropyranone derivatives have potential bioactivities. However, it is still undisclosed to prepare sulfoximide-substituted dihydropyranone derivatives. Herein, diphenyl phosphate, as Brønsted acid was used to catalyze the nucleophilic substitution reactions of sulfoximides and dihydropyranones to afford sulfoximide substituted dihydropyranone derivatives in 44%~78% yields. This method features mild conditions, simple operation and good functional group compatibility, which avoids using noble metals in traditional manners and provides a novel and effective strategy for the synthesis of glycosides.

Key words: Brønsted acid, sulfoximidie, dihydropyranone, glycoside

Cite this article

Xinhao Sun, Xuelun Duan, Wangze Song, Wenfeng Jiang. Brønsted Acid-Catalyzed the Synthesis of Sulfoximide Substituted Dihydropyranone Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 487-497.

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Entry	Catalyst (mol%)	Temp./℃	Solvent	Yield^b/%
1^c	[Ir(cod)Cl]₂ (2.5)	r.t.	CHCl₃	0
2^d	Pd(OAc)₂ (5)	r.t.	THF	33
3	(PhO)₂P(O)OH (50)	r.t.	CHCl₃	43
4	HCl (50)	r.t.	CHCl₃	26
5	TsOH (50)	r.t.	CHCl₃	15
6	TfOH (50)	r.t.	CHCl₃	18
7	TFA (50)	r.t.	CHCl₃	25
8	CsA (50)	r.t.	CHCl₃	38
9	PhCOOH (50)	r.t.	CHCl₃	0
10	(PhO)₂P(O)OH (50)	r.t.	DCM	41
11	(PhO)₂P(O)OH (50)	r.t.	DCE	38
12	(PhO)₂P(O)OH (50)	r.t.	Hexane	0
13	(PhO)₂P(O)OH (50)	r.t.	Toluene	33
14	(PhO)₂P(O)OH (50)	r.t.	THF	Trace
15	(PhO)₂P(O)OH (50)	r.t.	Acetone	24
16	(PhO)₂P(O)OH (50)	r.t.	MeCN	20
17	(PhO)₂P(O)OH (50)	r.t.	DMF	0
18	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	43
19	(PhO)₂P(O)OH (10)	r.t.	CHCl₃	38
20^e	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	57
21^f	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	58
22^f^,^g	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	68
23^f^,^h	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	64

Entry	Catalyst (mol%)	Temp./℃	Solvent	Yield^b/%
1^c	[Ir(cod)Cl]₂ (2.5)	r.t.	CHCl₃	0
2^d	Pd(OAc)₂ (5)	r.t.	THF	33
3	(PhO)₂P(O)OH (50)	r.t.	CHCl₃	43
4	HCl (50)	r.t.	CHCl₃	26
5	TsOH (50)	r.t.	CHCl₃	15
6	TfOH (50)	r.t.	CHCl₃	18
7	TFA (50)	r.t.	CHCl₃	25
8	CsA (50)	r.t.	CHCl₃	38
9	PhCOOH (50)	r.t.	CHCl₃	0
10	(PhO)₂P(O)OH (50)	r.t.	DCM	41
11	(PhO)₂P(O)OH (50)	r.t.	DCE	38
12	(PhO)₂P(O)OH (50)	r.t.	Hexane	0
13	(PhO)₂P(O)OH (50)	r.t.	Toluene	33
14	(PhO)₂P(O)OH (50)	r.t.	THF	Trace
15	(PhO)₂P(O)OH (50)	r.t.	Acetone	24
16	(PhO)₂P(O)OH (50)	r.t.	MeCN	20
17	(PhO)₂P(O)OH (50)	r.t.	DMF	0
18	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	43
19	(PhO)₂P(O)OH (10)	r.t.	CHCl₃	38
20^e	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	57
21^f	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	58
22^f^,^g	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	68
23^f^,^h	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	64

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