钯催化的磷、硫和硅中心手性化合物的合成进展

doi:10.6023/cjoc202208043

摘要/Abstract

含有磷、硫和硅三类杂原子中心手性的化合物在医药、农药、材料等领域有着广泛的应用, 高效构建这三类杂原子中心手性已经逐步发展成为不对称合成化学重要的前沿课题之一. 着重介绍了钯在手性配体或者助剂参与下, 高效构建磷、硫和硅中心手性化合物的方法. 在P中心手性构建方面, 主要从膦氢或膦-硅(氧)键活化、P中心去对称化以及环加成等策略进行介绍. 硫和硅中心手性化合物的发展稍晚, 合成策略有些类似. 对一些代表性的反应机理也做了介绍, 同时介绍了一些潜在的应用.

关键词: 钯催化, 磷手性, 硫手性, 硅手性, 不对称催化

Compounds bearing phosphorus, sulfur or silicon stereogenic center have a wide range of applications in the fields of medicine, pesticides, organic synthesis and material science. Efficient construction of these three types of heteroatom-centered chirality has gradually developed as one of the most important frontiers in asymmetric synthetic chemistry. This paper focuses on the recent development of the asymmetric synthesis via palladium/chiral complexes or using the chiral auxiliaries. Strategies such as P—X (X=H, Si or O) bond activation, desymmetrization, and cycloaddition for P-chiral compounds synthesis are introduced, while the methods for S and Si chiral compounds are somewhat similar. The mechanism of some representative examples and their potential applications are also included.

Key words: palladium catalysis, P-chirality, S-chirality, Si-chirality, asymmetric catalysis

引用此文

张洁明, 倪航, 吴起, 杨俊锋, 张俊良. 钯催化的磷、硫和硅中心手性化合物的合成进展[J]. 有机化学, 2022, 42(10): 3118-3128.

Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.

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图/表 25

图式1. 钯催化的不对称磷-氢键官能团化

Scheme 1. Pd-catalyzed asymmetric P—H functionalization

图式2. 消旋膦氢化合物的手性富集机理

Scheme 2. Proposed mechanism of the enantioselectivity enrichment of the racemic P-H compound

图式3. 膦氢化合物的动态动力学拆分机理实验

Scheme 3. Mechanistic study of DKR of P-H compounds

图式4. 消旋膦氢化合物的动态动力学拆分

Scheme 4. DKR of racemic P-H compounds

图式5. 钯催化的二级膦氧化合物(SPO)动态动力学拆分

Scheme 5. Pd-catalyzed DKR of SPO

图式6. 钯/DuPhos催化的炔烃不对称膦氢化反应

Scheme 6. Pd/DuPhos-catalyzed asymmetric hydrophosphination of alkynes

图式7. 钯/XiaoPhos催化的炔烃不对称膦氢化反应

Scheme 7. Pd/XiaoPhos-catalyzed asymmetric hydrophosphination of alkynes

图式8. 钯催化的不对称膦硅偶联反应

Scheme 8. Pd-catalyzed asymmetric P-Si coulpling

图式9. 钯催化的C—P键复分解反应

Scheme 9. Pd-catalyzed C—P bond metathesis

图式10. 钯催化的亚膦酰胺的手性转移反应

Scheme 10. Pd-catalyzed chirality transfer reaction of phosphoramidites

图式11. 钯催化的立体专一性C—P偶联反应

Scheme 11. Pd-Catalyzed stereospecific C—P coupling

图式12. 钯催化的磷中心化合物的去对称化反应

Scheme 12. Pd-catalyzed desymmetrization of P-stereogenic compounds

图式13. 钯催化的P中心不对称环加成反应

Scheme 13. Pd-catalyzed asymmetric cycloaddition of P-stereogenic compounds

图式14. 钯/Josiphos催化的亚磺酰基阴离子不对称芳基化反应

Scheme 14. Pd/Josiphos-catalyzed asymmetric arylation of sulfenate anions

图式15. 钯/PCphos催化的亚磺酰基阴离子不对称芳基化反应

Scheme 15. Pd/PCphos-catalyzed asymmetric arylation of sulfenate anions

图式16. 钯催化的亚磺酰基阴离子的不对称烯基化反应

Scheme 16. Pd-catalyzed asymmetric olefination of sulfenate anions

图式17. 钯催化的经由不对称C—H键烯基化的双芳基亚砜的平行动力学拆分和去对称化反应

Scheme 17. Pd-catalyzed asymmetric C—H olefination of diaryl sulfoxides through parallel kinetic resolution and desymmetrization

图式18. 钯催化的硫中心亚胺的动力学拆分

Scheme 18. Pd-catalyzed kinetic resolution of S-stereogenic imines

图式19. 钯催化的硅杂环丁烷的去对称化反应

Scheme 19. Pd-catalyzed desymmetrization of silacyclobutanes

图式20. 钯催化的分子间硅杂环丁烷的去对称化反应

Scheme 20. Pd-catalyzed intermolecular desymmetrization of silacyclobutanes

图式21. 基于DFT理论计算提出的钯催化的分子间硅杂环丁烷的去对称化反应机理

Scheme 21. Proposed mechanism of Pd-catalyzed desymmetrization of silacyclobutanes with alkynes to silicon-stereogenic silanes based on a density functional theory study

图式22. 钯催化的硅中心双苯基硅化合物的去对称化反应

Scheme 22. Pd-catalyzed desymmetration of Si-stereogenic dibenzosiloes

图式23. 钯催化的硅烷不对称芳基化反应

Scheme 23. Pd-catalyzed aymmetric arylation of silane

图式24. 配体结构对钯催化的硅烷不对称芳基化反应的影响分析

Scheme 24. Study of ligand structure for Pd-catalyzed asymmetric arylation of silane

图式25. 钯催化的硅烷去对称化反应

Scheme 25. Pd-catalyzed desymmetrization of silanes

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