动力学拆分在过渡金属催化的不对称(转移)氢化中的应用研究

doi:10.6023/cjoc202303001

摘要/Abstract

动力学拆分是一个经典的从外消旋化合物获得光学活性物质的策略, 而过渡金属催化的不对称(转移)氢化是高效和高原子经济性地合成手性化合物的方法. 将动力学拆分与不对称(转移)氢化相结合, 基于已开发的性能优良的过渡金属催化剂, 化学家们发展了结构多样的带有不同类型手性中心的不饱和化合物的动力学拆分-不对称(转移)氢化反应, 并将其应用于多类手性药物和天然产物的不对称合成中. 根据待氢化的不饱和键类型进行分类, 综述了该领域所取得的成果, 并对后续的发展进行了展望.

关键词: 动力学拆分, 不对称氢化, 不对称转移氢化, 过渡金属

Kinetic resolution (KR) has long been a popular and classical strategy in organic synthesis to obtain optically active compounds from racemic substrates, and transition metal catalyzed asymmetric (transfer) hydrogenation is a powerful method for the synthesis of chiral compounds with high efficiency and atom economy. Over the years, a large variety of unsaturated compounds bearing different types of chiral centers have been kinetically resolved with great efficiency via asymmetric (transfer) hydrogenation using some well-established chiral transition metal catalysts, and KR has been demonstrated to be a versatile technique in the synthesis of various chiral intermediates for biologically active compounds and natural products. The research progresses in this field are summarized. Moreover, the prospects of further developments are also discussed.

Key words: kinetic resolution, asymmetric hydrogenation, asymmetric transfer hydrogenation, transition metal

引用此文

褚杨杨, 韩召斌, 丁奎岭. 动力学拆分在过渡金属催化的不对称(转移)氢化中的应用研究[J]. 有机化学, 2023, 43(6): 1934-1951.

Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.

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图/表 23

图式1. 经典动力学拆分和选择性因子、动态动力学拆分及平行动力学拆分

Scheme 1. Classical kinetic resolution and selectivity factor, dynamic kinetic resolution and parallel kinetic resolution

图式2. 铑催化外消旋脱氢二肽1的动力学拆分-不对称氢化

Scheme 2. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic dehydrodipeptide 1

图式3. 铑催化的外消旋Morita-Baylis-Hillman加合物的动力学拆分-不对称(转移)氢化

Scheme 3. Rh catalyzed kinetic resolution-asymmetric (transfer) hydrogenation of racemic Morita-Baylis-Hillman adducts

图式4. 铑催化外消旋(杂)芳香醛衍生的MBH加合物的动力学拆分-不对称氢化

Scheme 4. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic (hetero) aromatic aldehyde-derived MBH adducts

图式5. 铑催化外消旋α,β-不饱和亚砜的动力学拆分-不对称氢化

Scheme 5. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic α,β-unsaturated sulfoxides

图式6. 铑催化外消旋乙烯基膦氧和次膦酸酯的动力学拆分-不对称氢化

Scheme 6. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic α,β-unsaturated phosphane oxides and phosphinate

图式7. 铑催化外消旋3,4-二取代1,4,5,6-四氢吡啶和1,4-二氢吡啶的动力学拆分-不对称氢化

Scheme 7. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic 3,4-disubstituted 1,4,5,6-tetrahydropyridines and 1,4-dihydropyridines

图式8. 钌催化外消旋烯丙醇的动力学拆分-不对称氢化

Scheme 8. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic allylic alcohols

图式9. 铱催化外消旋烯丙醇的动力学拆分-不对称氢化

Scheme 9. Ir catalyzed kinetic resolution-asymmetric hydrogenation of racemic allyl alcohols

图式10. 铑催化外消旋1-联芳基萘的动力学拆分-不对称氢化

Scheme 10. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic 1-aryl naphathalenes

图式11. 铑催化外消旋黄烷酮的动力学拆分-不对称转移氢化

Scheme 11. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic flavanones

图式12. 铑催化外消旋黄烷酮的动力学拆分-不对称转移氢化-脱氧化反应

Scheme 12. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation-deoxygenation of racemic flavanones

图式13. 铑催化外消旋乙酰基氮杂黄烷酮的动力学拆分-不对称转移氢化

Scheme 13. Rh catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic N-acetyl azaflavanones

图式14. 钌催化外消旋氮杂黄烷酮的动力学拆分-不对称氢化

Scheme 14. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic azaflavanones

图式15. 钌催化外消旋3-芳基-1-茚酮的动力学拆分-不对称转移氢化

Scheme 15. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of 3-aryl-1-indanones

图式16. 铱催化外消旋5-烷基-5-羟基戊酸酯的动力学拆分-不对称氢化

Scheme 16. Ir catalyzed kinetic resolution-asymmetric hydrogenation of racemic 5-alkyl-5-hydroxypentanoates

图式17. 钌催化外消旋二茂铁化合物35的动力学拆分-不对称转移氢化

Scheme 17. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic ferrocene based compound 35

图式18. 钌催化外消旋4-甲酰基-[2,2]-对环芳烷的动力学拆分-不对称转移氢化

Scheme 18. Ru catalyzed kinetic resolution-asymmetric transfer hydrogenation of racemic 4-formyl-[2,2]-paracyclophanes

图式19. 铑催化外消旋亚胺的动力学拆分-不对称氢化

Scheme 19. Rh catalyzed kinetic resolution-asymmetric hydrogenation of racemic imines

图式20. 钛催化外消旋二取代1-吡咯啉的动力学拆分-不对称氢化

Scheme 20. Ti catalyzed kinetic resolution-asymmetric hydrogenation of racemic disubstituted 1-pyrrolines

图式21. 钌催化外消旋2,3,3-三取代3H-吲哚的动力学拆分-不对称氢化

Scheme 21. Ru catalyzed kinetic resolution-asymmetric hydrogenation of racemic 2,3,3-trisubstituted 3H-indoles

图式22. 锰催化外消旋2,3,3-三取代3H-吲哚的动力学拆分-不对称氢化

Scheme 22. Mn catalyzed kinetic resolution-asymmetric hydrogenation of racemic 2,3,3-trisubstituted 3H-indoles

图式23. 镍催化外消旋[2.2]-对环芳烷衍生环状磺酰亚胺的动力学拆分-不对称氢化

Scheme 23. Ni catalyzed kinetic resolution-asymmetric hydrogenation of racemic-[2,2]-paracylophane-derived cyclic N-sulfonylimines

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