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

doi:10.6023/cjoc202208032

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3015-3032.DOI: 10.6023/cjoc202208032 Previous Articles Next Articles

Special Issue: 不对称催化专辑

ACCOUNT

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

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

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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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Fig. & Tab. 24

Scheme 1. Racemization mechanism of chiral thiiranium ion intermediates

Figure 1. Catalytic systems for enantioselective electrophilic sulfenylation reactions

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

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

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

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

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

Scheme 7. Enantioselective intermolecular three-component sulfenylations of alkenes

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

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

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

Scheme 11. Enantioselective intermolecular sulfenylation/methoxylation of alkenes

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

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

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

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

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

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

Scheme 17. Atroposelective sulfenylation of biaryl phenols containing naphthyl group

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

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

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

Scheme 20. Proposed mechanism of atroposelective sulfenylation of biaryl phenols

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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