手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用

doi:10.6023/cjoc202208032

有机化学 ›› 2022, Vol. 42 ›› Issue (10): 3015-3032.DOI: 10.6023/cjoc202208032 上一篇下一篇

所属专题：不对称催化专辑

研究专题

手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用

朱登^a^,^b, 陈志敏^a^,^b^,^*()

a 上海交通大学化学化工学院上海 200240
b 上海市手性药物分子工程重点实验室上海 200240

收稿日期:2022-08-24 修回日期:2022-09-18 发布日期:2022-11-02
通讯作者: 陈志敏

作者简介:

朱登, 2019年在浙江工业大学获得学士学位, 现为上海交通大学博士研究生, 导师为陈志敏副教授, 主要研究方向为手性含硫化合物的高效合成.

陈志敏, 博士, 长聘教轨副教授, 上海市高校特聘教授(东方学者). 2009年在福州大学获学士学位, 2014年在兰州大学获有机化学博士学位, 导师涂永强教授. 2014~2017年在上海交通大学(导师: 涂永强教授)从事博士后研究, 期间2015~2017在美国犹他大学(导师: Matthew S. Sigman教授)从事博士后研究. 2017年底加入上海交通大学化学化工学院, 开展独立研究, 主要围绕手性硫化学和硒化学开展研究工作, 通过发展新催化剂、新试剂、新策略实现各种手性硫化合物、硒化合物的高效合成.

基金资助:
国家自然科学基金(21871178); 国家自然科学基金(22071149); 上海市科学技术委员会(19JC1430100); 上海高校特聘教授(东方学者)资助项目

Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides

Deng Zhu^a^,^b, Zhi-Min Chen^a^,^b()

a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
b Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240

Received:2022-08-24 Revised:2022-09-18 Published:2022-11-02
Contact: Zhi-Min Chen
Supported by:
National Natural Science Foundation of China(21871178); National Natural Science Foundation of China(22071149); Science & Technology Department of Shanghai(19JC1430100); Program for Professor of Special Appointment(Eastern Scholar) at Shanghai Institutions of Higher Learning

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摘要/Abstract

手性含硫化合物不仅是有机合成领域重要的中间体和催化剂, 许多天然产物和临床药物也都是手性含硫化合物. 因此, 发展手性含硫化合物的高效合成方法一直是有机合成化学的重要研究课题, 其中不对称亲电硫化反应近年来受到化学家的广泛关注. 氢键相互作用可以在化合物的生成过程中提供很高的灵活性, 已经逐渐成为不对称催化中的有力工具. 受此启发, 本课题组开发了一类基于氢键相互作用的路易斯碱/布朗斯特酸协同催化策略, 并成功将其应用于多种类型烯烃的分子内和分子间的不对称芳硫基化反应, 以及芳基化合物的不对称芳硫基取代反应, 高效地合成了各种手性含硫化合物. 总结了我们课题组利用基于氢键相互作用的路易斯碱/布朗斯特酸协同催化策略在不对称亲电芳硫基化反应中的研究进展, 并对其未来发展进行了展望.

关键词: 氢键相互作用, 协同催化, 路易斯碱, 布朗斯特酸, 分子间反应, 烯烃双官能团化, 手性硫化合物, 阻转异构

Chiral organosulfur compounds are not only important synthetic intermediates and catalysts in the field of organic synthesis, but also widely exist in many natural products and clinical drugs. The development of efficient synthesis of chiral organosulfur compounds has always been an important research topic in organic synthetic chemistry, in which enantioselective electrophilic sulfenylation reactions have attracted significant attention in recent years. Hydrogen bond interactions provide much flexibility in the preorganization of compounds and have gradually become a powerful tool in asymmetric catalysis. Inspired from this, our group developed a type of Lewis base/Brønsted acid synergistic catalysis strategy based on the hydrogen bonding interaction, and successfully applied it to intra- and inter-molecular asymmetric sulfenylation of different kinds of alkenes, and enantioselective sulfenylation substitution reactions of aryl compounds. A variety of chiral organosulfur compounds were obtained with high efficiency. The recent advances of enantioselective electrophilic arylthiolation reactions using novel synergistic catalysis strategy developed by our group are summarized, and the prospect of this research topic is also discussed.

Key words: hydrogen bonding interaction, synergistic catalysis, Lewis base, Brønsted acid, intermolecular reaction, alkene difunctionalization, chiral sulfide, atropisomerism

引用此文

朱登, 陈志敏. 手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用[J]. 有机化学, 2022, 42(10): 3015-3032.

Deng Zhu, Zhi-Min Chen. Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3015-3032.

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图/表 24

图式1. 手性硫鎓离子消旋化的原因

Scheme 1. Racemization mechanism of chiral thiiranium ion intermediates

图1. 不对称亲电芳硫基化反应的催化体系

Figure 1. Catalytic systems for enantioselective electrophilic sulfenylation reactions

图式2. 1,1-二取代烯烃的不对称亲电芳硫基化反应

Scheme 2. Enantioselective electrophilic sulfenylation reactions of 1,1-disubstituted alkenes

图式3. 1,1-二取代烯丙醇的对映选择性芳硫基化/半频哪醇重排反应

Scheme 3. Enantioselective sulfenylation/semipinacol rearrangement of 1,1-disubstituted allylic alcohols

图式4. 三取代烯丙醇(茚骨架底物)的对映选择性芳硫基化/半频哪醇重排反应

Scheme 4. Enantioselective sulfenylation/semipinacol rearrangement of trisubstituted indene-type allylic alcohols

图式5. 反应中可能存在的催化活性物种的低温31P NMR谱实验

Scheme 5. Low-temperature 31P NMR experiments of proposed catalytically active species

图式6. 烯丙醇的对映选择性芳硫基化/半频哪醇重排反应的计算研究和可能的反应机理

Scheme 6. Computational studies and proposed mechanism of enantioselective sulfenylation/semipinacol rearrangement of allylic alcohol

图式7. 烯烃的不对称三组分分子间双官能化反应

Scheme 7. Enantioselective intermolecular three-component sulfenylations of alkenes

图式8. 烯烃的分子间不对称氧芳硫基化反应中苯酚衍生物的适用范围

Scheme 8. Substrate scope of phenol derivatives in enantioselective intermolecular oxysulfenylation of alkenes

图式9. 烯烃的分子间不对称氧芳硫基化反应中不同芳环底物的适用范围

Scheme 9. Substrate scope of different aryl groups in enantioselective intermolecular oxysulfenylation of alkenes

图式10. 烯烃的分子间不对称氧芳硫基化反应中不同官能团取代底物的适用范围

Scheme 10. Substrate scope of different functional groups in enantioselective intermolecular oxysulfenylation of alkenes

图式11. 烯烃的分子间不对称芳硫基化/甲氧基化反应

Scheme 11. Enantioselective intermolecular sulfenylation/methoxylation of alkenes

图式12. 烯烃的分子间不对称氧芳硫基化反应中醇类亲核试剂的适用范围

Scheme 12. Substrate scope of aliphatic alcohols in enantioselective intermolecular oxysulfenylation of alkenes

图式13. 手性硫化磷酰胺/手性磷酸共催化的烯烃不对称氧芳硫基化反应的可能机理

Scheme 13. Proposed mechanism of chiral sulfide/phosphoric acid cocatalyzed enantioselective oxysulfenylation of alkenes

图2. 基于BINOL骨架的手性Lewis碱硒化磷酰胺催化剂

Figure 2. Chiral Lewis basic selenide catalysts based on the BINOL framework

图式14. 手性路易斯碱和非手性磺酸协同催化的联芳基化合物的阻转选择性亲电芳硫基化反应

Scheme 14. Chiral Lewis base/achiral sulfonic acid cocatalyzed atroposelective sulfenylation of biaryl phenols

图式15. 可能的反应历程: 去对称化过程和动力学拆分过程

Scheme 15. Proposed reaction process: desymmetrization and kineticr esolution sequence

图式16. 联苯型双酚类化合物的阻转选择性芳硫基化及去对称化/动力学拆分反应

Scheme 16. Atroposelective sulfenylation of biaryl phenols via a desymmetrization/kinetic resolution sequence

图式17. 含稠环联芳基型双酚类化合物的阻转选择性芳硫基化反应

Scheme 17. Atroposelective sulfenylation of biaryl phenols containing naphthyl group

图18. 多苯环串联的双轴底物的阻转选择性芳硫基化反应

Scheme 18. Atroposelective sulfenylation of two-axis substrates with polyphenyl rings in series

图式19. 手性硒化磷酰胺催化剂结构对反应的影响

Scheme 19. Influence of different chiral Lewis basic selenide catalysts on the reaction

Entry	Acid	X	Yield/%	ee/%	pK_a (acid)
1	acid-1^a	0.1	79	92
2	No acid	0	67	0
3	acid-1	0.05	96	76
4	acid-1	0.2	76	87
5	acid-1	0.5	79	84
6	acid-1	1.0	59	82
7	acid-1 without C9	0.1	37	0
8	PTSA	0.1	71	90	-2.7
9	MSA	0.1	90	79
10	TfOH	0.1	70	49
11	TFA	0.1	73	18	-0.26
12	(PhO)₂P(O)OH	0.1	61	20	1.9
13	Benzoic acid	0.1	50	0	4.21
14	Acetic acid	0.1	75	0	4.8
15	Saccharin	0.1	56	0	2.2

表1. 不同类型非手性酸催化剂对反应的影响

Table 1. Influence of different achiral acid catalysts on the reaction

图式20. 联芳基化合物的亲电芳硫基化反应的可能机理

Scheme 20. Proposed mechanism of atroposelective sulfenylation of biaryl phenols

图3. 过渡态TS5和TS5'的非共价相互作用分析

Figure 3. Multiple noncovalent interactions of TS5 and TS5'

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手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用

Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides

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