Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮

doi:10.6023/cjoc202112040

有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1747-1758.DOI: 10.6023/cjoc202112040 上一篇下一篇

研究论文

Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮

张同利^a, 晏君^b, 何敬立^a, 寇学振^b, 申杰峰^a, 刘德龙^a^,^*(), 张万斌^a^,^b^,^*()

a 上海交通大学药学院上海市手性药物分子工程重点实验室上海 200240
b 上海交通大学化学化工学院教育部变革性分子前沿科学中心上海 200240

收稿日期:2021-12-29 修回日期:2022-02-21 发布日期:2022-03-03
通讯作者: 刘德龙, 张万斌
基金资助:
国家自然科学基金(21672142); 国家自然科学基金(21971162); 国家自然科学基金(21831005); 国家自然科学基金(21620102003); 上海市“超级博士后”激励计划(2020230); 中国博士后科学基金(2020M681276)

Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation

Tongli Zhang^a, Jun Yan^b, Jingli He^a, Xuezhen Kou^b, Jiefeng Shen^a, Delong Liu^a(), Wanbin Zhang^a^,^b()

a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
b Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2021-12-29 Revised:2022-02-21 Published:2022-03-03
Contact: Delong Liu, Wanbin Zhang
Supported by:
National Natural Science Foundation of China(21672142); National Natural Science Foundation of China(21971162); National Natural Science Foundation of China(21831005); National Natural Science Foundation of China(21620102003); Shanghai Post-Doctoral Excellence Program(2020230); China Postdoctoral Science Foundation(2020M681276)

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摘要/Abstract

利用轴手性Ir-BiphPHOX催化剂, 首次实现了5-芳基噁唑-2-酮的不对称催化氢化反应, 高收率、高选择性地合成了一系列手性5-芳基噁唑烷-2-酮类化合物. 该反应对多种官能团具有良好的相容性, 所得产物经简单转化可得到多种手性氨基醇类化合物或可衍生出具有生物活性的手性杂环化合物.

关键词: BiphPHOX, 不对称氢化, 5-芳基噁唑烷-2-酮, 手性, Ir-催化氢化

The enantioselective catalytic hydrogenation of 5-aryl-2-oxazolones has been achieved for the first time using the axially chiral Ir-BiphPHOX catalyst, providing the corresponding chiral 5-aryl-2-oxazolidinones in high yields and with excellent enantioselectivities. The protocol has good compatibility with a variety of functional groups, and the resulting products can be converted into various chiral amino alcohol compounds or can be transformed into a series of chiral heterocyclic compounds with various biological activities.

Key words: BiphPHOX, enantioselective hydrogenation, 5-aryl-2-oxazolidinone, chirality, Ir-catalyzed hydrogenation

引用此文

张同利, 晏君, 何敬立, 寇学振, 申杰峰, 刘德龙, 张万斌. Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮[J]. 有机化学, 2022, 42(6): 1747-1758.

Tongli Zhang, Jun Yan, Jingli He, Xuezhen Kou, Jiefeng Shen, Delong Liu, Wanbin Zhang. Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1747-1758.

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图/表 6

图1. 手性噁唑烷-2-酮结构以及2-氨基-1-苯基乙醇类药物

Figure 1. Chiral 2-oxazolidinones and 2-amino-1-phenylethanol drugs

图式1. 不对称催化氢化合成手性噁唑烷-2-酮

Scheme 1. Synthesis of chiral 2-oxazolidinones via enantioselective hydrogenation

图式2. 配体的筛选

Scheme 2. Screening of ligands Reaction conditions: 1a (31.5 mg, 0.1 mmol), molar ratio of substrate/catalyst (S/C) is 100, DCM (1 mL). Conversions were determined by 1H NMR, ee values were determined by HPLC using a Chiralcel AD-H column. The absolute conﬁguration of 2a was confirmed by X-ray diffraction analysis.

Entry	Solvent	p(H₂)/MPa	Temp./℃	Conv.^b/%	ee^c/%
1	DCM	5	30	97	87
2	DCE	5	30	>99	93
3	PhCl	5	30	58	93
4	Toluene	5	30	52	69
5	o-Xylene	5	30	34	85
6	THF	5	30	0	—
7	EtOAc	5	30	5	84
8	MeOH	5	30	0	—
9	DCE	4	30	93	91
10	DCE	6	30	>99	91
11	DCE	5	20	96	90
12	DCE	5	50	>99	90
13^d	DCE	5	30	82	93

表1. 溶剂?温度?压力和时间的筛选

Table 1. Screening of solvent, temperature, pressure and time

表2. 底物的拓展a

Table 2. Exploration of the substrates

图式3. 氢化产物的转化

Scheme 3. Transformation of the hydrogenated products

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Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮

Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation

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