醇与胺的不对称脱氢偶联升级反应研究进展

doi:10.6023/cjoc202207002

摘要/Abstract

手性醇及手性胺结构广泛存在于天然产物及药物分子中, 因而发展其不对称合成具有重要研究意义. 相较于传统方法, 过渡金属催化的醇与胺的不对称脱氢偶联制备高级手性醇和胺的反应具有优秀的步骤经济性、原子经济性及氧化还原经济性, 因而近年来得到了广泛的研究. 这类反应可从简单原料出发一步合成结构多样的手性醇与手性胺类化合物. 根据偶联试剂的种类进行划分, 总结了醇、胺参与的各类不对称脱氢偶联升级反应, 并对该领域的发展进行展望.

关键词: 手性醇, 手性胺, 不对称金属催化, 氢转移, 脱氢偶联, 碳碳成键反应

Chiral alcohol and amine are ubiquitous in natural products and pharmaceutically relevant molecules. Thus, developing the asymmetric synthesis of these molecules is of great importance. Compared with traditional methods, transition-metal-catalyzed asymmetric dehydrogenative coupling of alcohol and amine to advanced chiral alcohol and amine has been widely studied due to its excellent step-, atom- and redox-economy. This method allows for the one-step synthesis of structurally diverse chiral alcohol and chiral amine compounds from simple starting materials. Various types of asymmetric dehydrogenative coupling upgrading reactions involving alcohols and amines according to the types of coupling reagents are summarized and the outlook on the development of the field is provided.

Key words: chiral alcohol, chiral amine, asymmetric metal catalysis, hydrogen transfer, dehydrogenative coupling, carbon- carbon bond-forming reaction

引用此文

蒋滨阳, 施世良. 醇与胺的不对称脱氢偶联升级反应研究进展[J]. 有机化学, 2022, 42(10): 3263-3279.

Binyang Jiang, Shi-Liang Shi. Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3263-3279.

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图/表 21

图1. 含有手性醇或手性胺结构的药物及天然产物

Figure 1. Drugs and natural products containing chiral alcohol or amine

图式1. 合成手性醇及手性胺的几种方法

Scheme 1. Several methods for synthesizing chiral alcohol and amine

图式2. 铱催化的烯丙基醋酸酯与苄醇的不对称脱氢偶联

Scheme 2. Iridium-catalyzed asymmetric dehydrogenative coupling of allylic acetate and benzylic alcohol

图式3. 铱催化的α-甲基烯丙基醋酸酯与一级醇的不对称脱氢偶联

Scheme 3. Iridium-catalyzed asymmetric dehydrogenative coupling of α-methyl allylic acetate and primary alcohol

图式4. 铱催化的环氧乙烷与伯醇的不对称脱氢偶联

Scheme 4. Iridium-catalyzed asymmetric dehydrogenative coupling of epoxide and primary alcohol

图式5. 炔丙基亲电试剂与伯醇的不对称脱氢偶联

Scheme 5. Propargyl electrophile involved asymmetric dehydrogenative coupling with primary alcohol1

图式6. 钌催化的内炔与伯醇的不对称脱氢偶联

Scheme 6. Ruthenium-catalyzed asymmetric dehydrogenative coupling of internal alkyne and primary alcohol

图式7. 钌催化内炔与伯醇的不对称脱氢偶联催化循环

Scheme 7. Catalytic cycle of ruthenium-catalyzed asymmetric dehydrogenative coupling of internal alkyne and primary alcohol

图式8. 镍催化醇与炔烃的不对称脱氢偶联

Scheme 8. Nickel-catalyzed asymmetric dehydrogenative coupling of alkyne and alcohol

图式9. 钌催化伯醇与2-硅基丁二烯的不对称脱氢偶联

Scheme 9. Ruthenium-catalyzed asymmetric dehydrogenative coupling of 2-silyl-butadiene and primary alcohol

图式10. 钌催化伯醇与丁二烯的不对称脱氢偶联

Scheme 10. Ruthenium-catalyzed asymmetric dehydrogenative coupling of butadiene and primary alcohol

图式11. 伯醇与各类官能化联烯的不对称脱氢偶联

Scheme 11. Asymmetric dehydrogenative coupling of primary alcohol and various functionalized allene

图式12. 伯醇与烯炔的不对称脱氢偶联

Scheme 12. Asymmetric dehydrogenative coupling of primary alcohol and enyne

图式13. 烯丙醇与芳基硼酸的不对称脱氢偶联

Scheme 13. Asymmetric dehydrogenative coupling of allylic alcohol and aryl boronic acid

图式14. 镍催化的仲醇与芳基硼酸酯的不对称脱氢偶联

Scheme 14. Nickel-catalyzed asymmetric dehydrogenative coupling of secondary alcohol and aryl boronic ester

图式15. 铱催化的一级醇与环丙烷的不对称脱氢偶联

Scheme 15. Iridium-catalyzed asymmetric dehydrogenative coupling of primary alcohol and cyclopropane

图式16. 钌催化的苯并环丁酮与α-羟基酮的不对称脱氢偶联

Scheme 16. Ruthenium-catalyzed asymmetric dehydrogenative coupling of benzocyclobutenone and ketol

图式17. 钌催化的不对称Guerbet反应

Scheme 17. Ruthenium-catalyzed asymmetric Guerbet reaction

图式18. 钽催化的四氢喹啉与降冰片烯的不对称脱氢偶联

Scheme 18. Tantalum-catalyzed asymmetric dehydrogenative coupling of tetrahydroquinoline and norbornene

图式19. 镍催化的胺与内炔的不对称脱氢偶联

Scheme 19. Nickel-catalyzed asymmetric dehydrogenative coupling of amine and internal alkyne

图式20. 镍催化的胺与苯乙烯的不对称脱氢偶联

Scheme 20. Nickel-catalyzed asymmetric dehydrogenative coupling of amine and styrene

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