Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters

doi:10.6023/cjoc202111030

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1520-1526.DOI: 10.6023/cjoc202111030 Previous Articles Next Articles

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手性方酰胺催化环状1,3-二羰基化合物对β,γ-不饱和-α-酮酯的不对称Michael加成反应

马志伟^a^,^*(), 陈晓培^a, 王川川^a, 王建玲^a, 陶京朝^b, 吕全建^a^,^*()

a 河南牧业经济学院理学部郑州 450046
b 郑州大学化学学院郑州 450001

收稿日期:2021-11-22 修回日期:2022-01-02 发布日期:2022-01-20
通讯作者: 马志伟, 吕全建
作者简介:
^†共同第一作者
基金资助:
河南省自然科学基金(202300410188); 河南省高等学校青年骨干教师培养计划(2021GGJS173)

Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters

Zhiwei Ma^a(), Xiaopei Chen^a, Chuanchuan Wang^a, Jianling Wang^a, Jingchao Tao^b, Quanjian Lü^a()

a Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
b College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2021-11-22 Revised:2022-01-02 Published:2022-01-20
Contact: Zhiwei Ma, Quanjian Lü
About author:
^†These authors contributed equally to this work
Supported by:
Natural Science Foundation of Henan Province(202300410188); Training Plan for Young Key Teachers in Colleges and Universities in Henan Province(2021GGJS173)

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Abstract

A stereoselective methodology was developed to construct synthetically and pharmaceutically useful chiral chromene derivatives. In the presence of a newly designed bifunctional tertiary amine-squaramide organocatalyst, the Michael addition between cyclic 1,3-diketones and β,γ-unsaturated α-ketoesters occurred smoothly to provide the desired products with high to excellent yields (84%~97%) and enantioselectivies (79%~97% ee). This catalytic protocol was compatible with a range of structurally distinct β,γ-unsaturated α-ketoesters.

Key words: Michael addition, organocatalysis, tertiary amine-squaramide, cyclic diketone, β,γ-unsaturated α-ketoesters

Cite this article

Zhiwei Ma, Xiaopei Chen, Chuanchuan Wang, Jianling Wang, Jingchao Tao, Quanjian Lü. Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1520-1526.

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Fig. & Tab. 7

References 13

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Entry	Solvent	Yield^b/%	ee^c/%
1	CH₂Cl₂	94	83
2	Et₂O	93	85
3	THF	89	77
4	Toluene	91	71
5	CH₃OH	46	20
6^d	Et₂O	95	91
7^e	Et₂O	76	91
8^f	Et₂O	70	90

Entry	Solvent	Yield^b/%	ee^c/%
1	CH₂Cl₂	94	83
2	Et₂O	93	85
3	THF	89	77
4	Toluene	91	71
5	CH₃OH	46	20
6^d	Et₂O	95	91
7^e	Et₂O	76	91
8^f	Et₂O	70	90

Entry	R¹ (5)	R², R³ (6)	7	Yield^b/%	ee^c/%
1	H (5a)	Ph, CH₃(6a)	7a	95	91
2	H (5a)	4-CH₃C₆H₄, CH₃(6b)	7b	93	86
3	H (5a)	4-CH₃OC₆H₄, CH₃(6c)	7c	93	90
4	H (5a)	4-FC₆H₄, CH₃(6d)	7d	90	87
5	H (5a)	4-ClC₆H₄, CH₃(6e)	7e	91	88
6	H (5a)	4-BrC₆H₄, CH₃(6f)	7f	92	86
7	H (5a)	2-Thienyl, CH₃(6g)	7g	85	82
8	H (5a)	2-Naphthyl, CH₃(6h)	7h	86	88
9	H (5a)	Ph, Bn (6i)	7i	97	89
10	CH₃ (5b)	Ph, CH₃(6a)	8a	95	97
11	CH₃ (5b)	4-CH₃C₆H₄, CH₃(6b)	8b	92	90
12	CH₃ (5b)	4-CH₃OC₆H₄, CH₃(6c)	8c	93	90
13	CH₃ (5b)	4-FC₆H₄, CH₃(6d)	8d	94	84
14	CH₃ (5b)	4-ClC₆H₄, CH₃(6e)	8e	91	89
15	CH₃ (5b)	4-BrC₆H₄, CH₃(6f)	8f	91	79
16	CH₃ (5b)	2-Thienyl, CH₃(6g)	8g	87	84
17	CH₃ (5b)	2-Naphthyl, CH₃(6h)	8h	84	88
18	CH₃ (5b)	Ph, Bn (6i)	8i	94	88
19	CH₃ (5b)	Ph, Et (6j)	8j	95	84
20	CH₃ (5b)	Et, Et (6k)	8k	93	80

Entry	R¹ (5)	R², R³ (6)	7	Yield^b/%	ee^c/%
1	H (5a)	Ph, CH₃(6a)	7a	95	91
2	H (5a)	4-CH₃C₆H₄, CH₃(6b)	7b	93	86
3	H (5a)	4-CH₃OC₆H₄, CH₃(6c)	7c	93	90
4	H (5a)	4-FC₆H₄, CH₃(6d)	7d	90	87
5	H (5a)	4-ClC₆H₄, CH₃(6e)	7e	91	88
6	H (5a)	4-BrC₆H₄, CH₃(6f)	7f	92	86
7	H (5a)	2-Thienyl, CH₃(6g)	7g	85	82
8	H (5a)	2-Naphthyl, CH₃(6h)	7h	86	88
9	H (5a)	Ph, Bn (6i)	7i	97	89
10	CH₃ (5b)	Ph, CH₃(6a)	8a	95	97
11	CH₃ (5b)	4-CH₃C₆H₄, CH₃(6b)	8b	92	90
12	CH₃ (5b)	4-CH₃OC₆H₄, CH₃(6c)	8c	93	90
13	CH₃ (5b)	4-FC₆H₄, CH₃(6d)	8d	94	84
14	CH₃ (5b)	4-ClC₆H₄, CH₃(6e)	8e	91	89
15	CH₃ (5b)	4-BrC₆H₄, CH₃(6f)	8f	91	79
16	CH₃ (5b)	2-Thienyl, CH₃(6g)	8g	87	84
17	CH₃ (5b)	2-Naphthyl, CH₃(6h)	8h	84	88
18	CH₃ (5b)	Ph, Bn (6i)	8i	94	88
19	CH₃ (5b)	Ph, Et (6j)	8j	95	84
20	CH₃ (5b)	Et, Et (6k)	8k	93	80

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手性方酰胺催化环状1,3-二羰基化合物对β,γ-不饱和-α-酮酯的不对称Michael加成反应

Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters

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