不对称催化构建硅立体中心化合物的新反应体系研究进展

doi:10.6023/cjoc202306027

摘要/Abstract

过去二十年以来, 硅立体中心手性有机硅化合物在有机合成、材料科学和药物设计等领域引起了广泛关注. 然而, 有机硅化合物的来源局限性大大限制了其在这些领域的应用拓展. 因此, 发展高效、高选择性的不对称催化合成方法以获得硅立体中心手性有机硅化合物是亟需解决的挑战性难题. 主要综述了2011年以来通过不对称催化合成硅立体中心手性有机硅化合物的最新研究进展.

关键词: 硅立体中心, 过渡金属催化, 有机硅化合物, 不对称催化

In the past two decades, organosilicon compounds bearing silicon-stereogenic centers have attracted extensive attention in the fields of organic synthesis, materials, and drug design. However, the expansion of organosilicon compounds in these fields has been greatly restricted by limited source of organosilicon compounds. Therefore, the development of highly efficient and selective asymmetric catalytic methods to obtain chiral organosilicon compounds with silicon-stereogenic centers is a challenging task that needs to be solved urgently. The latest research progress on new catalytic reaction systems for asymmetric synthesis of silicon-stereogenic center containing organosilanes since 2011 is mainly summarized.

Key words: silicon-stereogenic center, transition-metal catalysis, organosilicon compounds, asymmetric catalysis

引用此文

曾燕, 叶飞. 不对称催化构建硅立体中心化合物的新反应体系研究进展[J]. 有机化学, 2023, 43(10): 3388-3413.

Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.

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图/表 81

图式1. 不对称催化构建硅立体中心的最新研究进展概要

Scheme 1. Summary of research progress on asymmetric construction of silicon-stereogenic center

图式2. 二氯硅烷对映选择性醇解反应

Scheme 2. Enantioselective alcoholysis reaction of dichlorosilane

图式3. Pt催化二氢硅烷的串联反应

Scheme 3. Pt-catalyzed tandem reaction of dihydrosilanes

图式4. 铂催化的二氢硅烷串联氢化硅烷化/环化反应

Scheme 4. Platinum-catalyzed tandem hydrosilylation/cycliza- tion with dihydrosilanes

图式5. 铑催化二氢硅烷的脱氢Si—O偶联反应

Scheme 5. Rhodium-catalyzed dehydrogenative Si—O coupling reaction

图式6. 铑催化二氢硅烷的不对称水解氧化反应

Scheme 6. Rhodium-catalyzed asymmetric hydrolysis oxidation of dihydrosilanes

图式7. 铜催化二氢硅烷的不对称水解氧化反应

Scheme 7. Copper-catalyzed asymmetric hydrolysis oxidation of dihydrosilanes

图式8. 铑催化二氢硅烷的脱氢Si—N偶联反应

Scheme 8. Rhodium-catalyzed dehydrogenative Si—N coupling reaction

图式9. 铑催化亚砜亚胺与二氢硅烷的不对称交叉偶联反应

Scheme 9. Rhodium-catalyzed asymmetric cross-coupling reaction of sulfoxide imines and dihydrosilanes

图式10. 铑催化双(烯基)二氢硅烷的分子内硅氢加成反应

Scheme 10. Rhodium-catalyzed intramolecular hydrosilylation of bis(alkenyl)dihydrosilanes

图式11. 铑催化硅桥连双烯的分子内硅氢加成反应

Scheme 11. Rhodium-catalyzed intramolecular hydrosilylation of silicon-bridged dienes

图式12. 铑催化二烯烃分子内硅氢加成反应

Scheme 12. Rhodium-catalyzed intramolecular hydrosilylation of dienes

图式13. 对映选择性合成硅手性中心单氢硅烷

Scheme 13. Enantioselective synthesis of silicon-stereogenic monohydrosilanes

图式14. 钪催化分子间烯烃氢化硅烷化

Scheme 14. Scandium-catalyzed intermolecular alkene hydrosilylation

图式15. 铑催化末端烯烃的不对称硅氢加成反应

Scheme 15. Rhodium-catalyzed asymmetric hydrosilylation of terminal alkenes

图式16. 钴催化1,3-共轭二烯的硅氢加成反应

Scheme 16. Cobalt-catalyzed hydrosilylation of 1,3-dienes

图式17. 铑催化环丙烯的去对称化硅氢加成反应

Scheme 17. Rhodium-catalyzed desymmetric hydrosilylation of cyclopropenes

图式18. 铂催化的炔烃的不对称硅氢加成

Scheme 18. Platinum-catalyzed asymmetric hydrosilylation of alkynes

图式19. 钴催化炔烃的不对称硅氢加成反应

Scheme 19. Cobalt-catalyzed asymmetric hydrosilylation of alkynes

图式20. 钯催化炔酮的不对称硅氢加成反应

Scheme 20. Palladium-catalyzed asymmetric hydrosilylation of ynones

图式21. 钯催化二炔的不对称硅氢加成反应

Scheme 21. Palladium-catalzyed asymmetric hydrosilylation of 1,3-diynes

图式22. 钴催化1,3-烯炔类化合物的硅氢加成反应

Scheme 22. Cobalt-catalyzed asymmetric hydrosilylation of 1,3-enynes

图式23. 铜催化的1,3-烯炔的对映选择性1,4-硅氢加成反应

Scheme 23. Copper-catalyzed asymmetric 1,4-hydrosilylation of 1,3-enynes

图式24. 铑催化前手性炔烃的分子内硅氢加成反应

Scheme 24. Rhodium-catalyzed intramolecular hydrosilylation of prochiral alkynes

图式25. 铑催化单氢硅烷的动态动力学转化反应

Scheme 25. Rhodium-catalyzed dynamic kinetic asymmetric hydrosilylation of monohydrosilanes

图式26. 钌催化重氮化合物的不对称Si—H插入反应

Scheme 26. Ruthenium-catalyzed asymmetric Si—H insertion reaction of diazo compounds

图式27. 铑催化双芳基卡宾的不对称Si—H插入反应

Scheme 27. Rhodium-catalyzed asymmetric Si—H insertion reaction of diarylcarbenes

图式28. 铑催化二氢硅烷分子内C(sp2)—H键硅基化环化反应

Scheme 28. Rhodium-catalyzed intramolecular C(sp2)—H bond silylation of dihydrosilanes

图式29. 铑催化二氢硅烷分子内C(sp3)—H键硅基化环化反应

Scheme 29. Rhodium-catalyzed intramolecular C(sp3)—H bond silylation of dihydrosilanes

图式30. 铑催化硅杂环丁烷开环/环化串联反应

Scheme 30. Rhodium-catalyzed ring-opening/cyclization tandem reaction of silacyclobutanes

图式31. 铑催化串联不对称C(sp2)—H键硅基化/烯烃硅氢加成反应

Scheme 31. Rhodium-catalyzed asymmetric C(sp2)—H bond silylation/alkene hydrosilylation reaction

图式32. 铑催化分子内不对称C(sp2)—H键脱氢硅基化反应

Scheme 32. Rhodium-catalyzed intramolecular asymmetric C(sp2)—H bond dehydrosilylation

图式33. 铑催化脱氢硅烷化合成二苯并共轭硅杂环化合物

Scheme 33. Synthesis of conjugated silicon heterocyclic compounds via rhodium-catalyzed dehydrosilylation

图式34. 铑催化不对称脱氢硅烷化合成单氢硅烷

Scheme 34. Enantioselective synthesis of monohydrosilane via rhodium-catalyzed asymmetric dehydrosilylation

图式35. 铑催化脱氢硅基化反应合成二氢苯并噻咯

Scheme 35. Synthesis of dihydrobenzosilole by rhodium-catal- yzed dehydrosilylation

图式36. 铑催化分子内C(sp3)—H键不对称脱氢硅基化反应

Scheme 36. Rhodium-catalyzed intramolecular dehydrogenative C(sp3)—H silylation

图式37. 铱催化分子内对映选择性脱硅基化反应

Scheme 37. Iridium-catalyzed intramolecular enantioselctive dehydrosilylation

图式38. 铑催化杂芳环的分子间C—H硅基烷化反应

Scheme 38. Rhodium-catalyzed intermolecular C—H silylation reaction of heteroarenes

图式39. 铑催化二氢硅烷与杂环芳烃的脱氢硅基化反应

Scheme 39. Rhodium-catalyzed dehydrosilylation of dihydro- silanes with heteroarenes

图式40. 钯催化碘代芳烃与二氢硅烷的交叉偶联反应

Scheme 40. Palladium-catalyzed cross-coupling reaction of iodoarenes with dihydrosilanes

图式41. 钯催化炔基溴化物和氢硅烷的交叉偶联反应

Scheme 41. Palladium-catalyzed cross-coupling reactions of alkynyl bromides with dihydrosilanes

图式42. 钯催化硅杂环丁烷对映选择性去对称化

Scheme 42. Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes

图式43. 钯催化硅杂环丁烷与内炔烃的对映选择性去对称化

Scheme 43. Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with internal alkynes

图式44. 铑催化硅杂环丁烷与端炔的对映选择性去对称化

Scheme 44. Rhodium-catalyzed enantioselective desymmetrization of silacyclobutanes with terminal alkynes

图式45. 铑催化C—Si键活化的三平面模型

Scheme 45. Three-layer chirality relay model in Rh(I)-catalyzed C—Si bond activation reaction

图式46. 含硅立体中心(-)-sila-mesembranol的不对称全合成

Scheme 46. Asymmetric total synthesis of (-)-silamesembra- nol bearing silicon-stereogenic center

图式47. 铑催化螺硅杂双环丁烷的不对称开环扩环反应

Scheme 47. Rhodium-catalyzed asymmetric ring expansion reaction of spirosilabicyclobutanes

图式48. 铑催化4/5-螺硅杂芴与炔烃的不对称扩环反应

Scheme 48. Rhodium-catalyzed asymmetric ring expansion of 4/5-spirosilafluorenes with alkynes

图式49. 钯催化硅杂环丁烷与丙二烯的不对称扩环反应

Scheme 49. Palladium-catalyzed asymmetric ring expansion reaction of silacyclobutanes with allenes

图式50. Rh/Cu共催化的硅杂环丁烷与炔基酯的[4＋2]环加成反应

Scheme 50. Rh/Cu-catalyzed [4＋2] annulation of silacyclobutanes and alkynyl esters

图式51. 镍催化硅杂环丁烷开环扩环反应

Scheme 51. Nickel-catalyzed ring-opening and ring-expansion reaction of silacyclobutanes

图式52. 镍催化硅杂环丁烷与炔烃的开环扩环反应

Scheme 52. Nickel-catalyzed ring-opening and ring-expansion reaction of silacyclobutanes with alkynes

图式53. 铑催化杂芳烃的分子间的C—H硅基化

Scheme 53. Rhodium-catalyzed intermolecular C—H silylation of heteroarenes

图式54. 铑催化不对称合成二芳基并硅醚

Scheme 54. Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines

图式55. 铑催化碳硅键活化合成苯并噻咯衍生物

Scheme 55. Rhodium-catalyzed activation of carbon silicon bonds to synthesize benzothiazole derivatives

图式56. 镍催化对映体和双立体选择性合成苯并噻咯衍射物

Scheme 56. Nickel-catalyzed enantioselective synthesis of benzoxasilole derivatives

图式57. 铑催化不对称内炔烃的炔基硅基化反应

Scheme 57. Rhodium-catalyzed asymmetric intramolecular alkynylsillaytion of alkynes

图式58. 铑催化硅杂芴开环/酰基化构建硅立体中心

Scheme 58. Rhodium-catalyzed ring opening/acylation of sila- fluorene to construct silicon-stereogenic center

图式59. 钯催化多芳基硅烷C(sp2)—H键芳基化反应构建硅立体中心

Scheme 59. Palladium catalyzed C(sp2)—H arylation reaction of polyarylsilanes

图式60. 钯催化对映体选择性1,5-钯迁移合成硅立体中心5,10-二氢苯氮杂硅烷

Scheme 60. Palladium-catalyzed synthesis of silicon-stereo- genic 5,10-dihydrophenazasilines via enantioselective 1,5-palla- dium migration

图式61. 钯催化碳氢键烯基化反应合成硅立体中心四取代有机硅烷化合物

Scheme 61. Palladium catalyzed olefinization of C(sp2)—H to synthesize tetrasubstituted organic silane compounds bearing silicon- stereogenic center

图式62. 铑催化[2＋2＋2]环加成反应构建硅立体中心

Scheme 62. Rhodium-catalyzed [2＋2＋2] cycloaddition reaction to construct silicon-stereogenic center

图式63. 铑催化[2＋2＋2]环加成反应合成轴手性硅螺环化合物

Scheme 63. Rhodium-catalyzed [2＋2＋2] cycloaddition to construct silicon-containing spiro compounds

图式64. 铂催化二炔基硅烷与联硼酸频哪醇酯的双硼化反应

Scheme 64. Platinum-catalyzed diboration reaction of dialkynylsilane with pinacol diborate

图式65. 铜催化硅基二醇的去对称化单酯化反应

Scheme 65. Copper-catalyzed desymmetrization monoesterification of silicone-bridged diols

图式66. 铜催化的硅二醇去对称化硅氧脱氢偶联反应

Scheme 66. Copper-catalyzed desymmetrization of silanediols

图式67. 铜催化烯基硅烷的硼氢化反应

Scheme 67. Copper-catalyzed desymmetrizing protoboration of vinylsilanes

图式68. 钯催化Heck环化反应构建硅桥连双环[3.2.1]化合物

Scheme 68. Palladium-catalyzed Heck cyclization reaction to construct silicon-bridged bicyclic [3.2.1] compounds

图式69. 钪催化硅杂环己酮的扩环三氟甲基化反应

Scheme 69. Scandium-catalyzed ring-expansion trifluoromethylation of silacyclohexanones

图式70. 镍催化[4＋1]硅杂环加成反应

Scheme 70. Nickel-catalyzed [4＋1] Sila-cycloaddition reaction

图式71. 有机催化偕二硅醇去对称化构建硅立体中心

Scheme 71. Organocatalytic desymmetrization of geminal disilanol to construct silicon stereocenters

图式72. 有机催化偕二烯丙基硅烷去对称化构建硅立体中心

Scheme 72. Organocatalytic desymmetrization of diallylsilane to construct silicon stereocenters

图式73. 有机催化动态动力学转化构建硅立体中心

Scheme 73. Construction of silicon stereocenters through organocatalytic dynamic kinetic asymmetric transformation

图式74. NHC催化硅桥连二醛的去对称化反应

Scheme 74. N-Heterocyclic carbene-catalyzed desymmetrization of silicon-bridged dibenzaldehydes

图式75. NHC催化硅桥连二醛的单酯化反应

Scheme 75. N-Heterocyclic carbene-catalyzed monoesterification of silicone-bridged dialdehydes

图式76. NHC催化二醛分子内安息香缩合反应

Scheme 76. Carbene-catalyzed desymmetric benzoin reaction of siladials

图式77. 异硫脲催化硅桥连双酚的酰化去对称化

Scheme 77. Isothiourea-catalyzed acylative desymmetrization of silicon-centered bisphenols

图式78. CPA催化不对称芳香环胺化反应构建硅立体中心

Scheme 78. Construction of silicon stereocenters through CPA-catalyzed asymmetric aromatic cyclic amination reaction

图式79. 不对称烯胺催化前手性硅烷的分子内醛缩反应

Scheme 79. Asymmetric enamine-catalyzed desymmetric intramolecular aldolization of prochiral siladials

图式80. 有机催化前手性硅二醇的基团选择性亲电硅烷化反应

Scheme 80. Organocatalytic group-selective electrophilic silylation of prochiral silanediols

图式81. 有机催化去对称化/Peterson烯基化反应

Scheme 81. Organocatalytic desymmetry/Peterson alkylation reaction

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