Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds

doi:10.6023/cjoc202306027

Abstract

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

Cite this article

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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Fig. & Tab. 81

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

Scheme 2. Enantioselective alcoholysis reaction of dichlorosilane

Scheme 3. Pt-catalyzed tandem reaction of dihydrosilanes

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

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

Scheme 6. Rhodium-catalyzed asymmetric hydrolysis oxidation of dihydrosilanes

Scheme 7. Copper-catalyzed asymmetric hydrolysis oxidation of dihydrosilanes

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

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

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

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

Scheme 12. Rhodium-catalyzed intramolecular hydrosilylation of dienes

Scheme 13. Enantioselective synthesis of silicon-stereogenic monohydrosilanes

Scheme 14. Scandium-catalyzed intermolecular alkene hydrosilylation

Scheme 15. Rhodium-catalyzed asymmetric hydrosilylation of terminal alkenes

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

Scheme 17. Rhodium-catalyzed desymmetric hydrosilylation of cyclopropenes

Scheme 18. Platinum-catalyzed asymmetric hydrosilylation of alkynes

Scheme 19. Cobalt-catalyzed asymmetric hydrosilylation of alkynes

Scheme 20. Palladium-catalyzed asymmetric hydrosilylation of ynones

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

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

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

Scheme 24. Rhodium-catalyzed intramolecular hydrosilylation of prochiral alkynes

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 37. Iridium-catalyzed intramolecular enantioselctive dehydrosilylation

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

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

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

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

Scheme 42. Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 56. Nickel-catalyzed enantioselective synthesis of benzoxasilole derivatives

Scheme 57. Rhodium-catalyzed asymmetric intramolecular alkynylsillaytion of alkynes

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

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

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

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

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

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

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

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

Scheme 66. Copper-catalyzed desymmetrization of silanediols

Scheme 67. Copper-catalyzed desymmetrizing protoboration of vinylsilanes

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

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

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

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

Scheme 72. Organocatalytic desymmetrization of diallylsilane to construct silicon stereocenters

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

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

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

Scheme 76. Carbene-catalyzed desymmetric benzoin reaction of siladials

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

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

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

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

Scheme 81. Organocatalytic desymmetry/Peterson alkylation reaction

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