Catalytic Enantioselective Preparation of Chiral Allylsilanes

doi:10.6023/cjoc202304030

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3367-3387.DOI: 10.6023/cjoc202304030 Previous Articles Next Articles

Special Issue: 有机硅化学专辑-2023

手性烯丙基硅烷的催化对映选择性合成

匡鑫^a^,^b, 丁昌华^a, 吴奕晨^b^,^*(), 王鹏^b^,^c^,^d^,^*()

a 上海大学理学院上海 201900
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 中国科学院上海有机化学研究所中国科学院能量调控材料重点实验室上海 200032
d 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024

收稿日期:2023-04-21 修回日期:2023-05-11 发布日期:2023-05-23
基金资助:
国家重点研发计划(2021YFA1500200); 国家自然科学基金(22101291); 国家自然科学基金(22171277); 国家自然科学基金(21821002); 上海“启明星”(20QA1411400)

Catalytic Enantioselective Preparation of Chiral Allylsilanes

Xin Kuang^a^,^b, Changhua Ding^a, Yichen Wu^b(), Peng Wang^b^,^c^,^d()

a College of Science, Shanghai University, Shanghai 201900
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
d School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Received:2023-04-21 Revised:2023-05-11 Published:2023-05-23
Contact: *E-mail: ywu@sioc.ac.cn; pengwang@sioc.ac.cn
Supported by:
National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(22101291); National Natural Science Foundation of China(22171277); National Natural Science Foundation of China(21821002); Shanghai Rising-Star Program(20QA1411400)

Chiral allylsilanes, a versatile linchpin, are widely used in the area of asymmetric synthesis. Therefore, the development of efficient methodologies for the preparation of the enantioenriched allylsilanes has attracted great attention. Significant advances have been made in the catalytic enantioselective preparation of chiral allylsilanes by virtue of the rapid developments in asymmetric catalysis. The advances in the construction of chiral allylsilanes and their synthetic applications are summarized.

Key words: chiral allylsilanes, asymmetric catalysis, catalytic synthesis

Cite this article

Xin Kuang, Changhua Ding, Yichen Wu, Peng Wang. Catalytic Enantioselective Preparation of Chiral Allylsilanes[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3367-3387.

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Fig. & Tab. 41

Scheme 1. Catalytic enantioselective preparation of chiral allylsilanes

Scheme 2. Early examples on Pd-catalyzed asymmetric hydrosilylation

Scheme 3. Pd-catalyzed asymmetric hydrosilylation with di- fluoro(phenyl)silane

Scheme 4. Pd-catalyzed asymmetric hydrosilylation using chiral (β-N-sulfonylaminoalkyl)phosphine ligand

Scheme 5. Pd-catalyzed asymmetric hydrosilylation using P-menthylphosphetane ligand

Scheme 6. Pd-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes with monodentate phosphine ligand

Scheme 7. Pd-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes with chiral phosphoramidite ligands

Scheme 8. Pd-catalyzed asymmetric hydrosilylation with 1,3-dienes

Scheme 9. Pd-catalyzed asymmetric hydrosilylation with acyclic 1,3-diene

Scheme 10. Pd-catalyzed asymmetric hydrosilylation with 1,3-dienes

Scheme 11. Co-catalyzed asymmetric hydrosilylation with 1,3-dienes

Scheme 12. Co-catalyzed asymmetric hydrosilylation of 1,3- dienes for the construction of Si-stereogenic allylsilanes

Scheme 13. Pd- and Cu-catalyzed asymmetric hydrosilylation of allenes

Scheme 14. Synthesis of chiral α-tertiary allylsilanes via nickel/SPSiPO catalyzed hydrosilylation

Scheme 15. Palladium-catalyzed asymmetric allylic substitution with disilanes

Scheme 16. Cu-1 catalyzed asymmetric allylic substitution

Scheme 17. Cu-2 catalyzed asymmetric Si-allylic substitution

Scheme 18. Asymmetric Si-allylic substitution with McQuade’s catalyst

Scheme 19. Cu/L20-catalyzed asymmetric allylic substitution

Scheme 20. Synthesis of chiral allylsilanes with bis(triorganosilyl)zinc compounds

Scheme 21. Catalytic enantioselective silyl-substitution with trifluoromethyl alkenes

Scheme 22. Asymmetric reduction of the γ-silylated allylic alcohol derivatives

Scheme 23. Cu-catalyzed asymmetric allylic substitution with organozinc reagents

Scheme 24. Cu-catalyzed asymmetric allylic substitution with Si-containing allyl partners

Scheme 25. Palladium-catalyzed asymmetric Kumada-type alkenylation

Scheme 26. Nickel-catalyzed enantioselective reductive alkenylation of α-chloro benzylsilanes

Scheme 27. CuH/Pd-catalyzed asymmetric hydroalkenylation of vinyl metalloids

Scheme 28. Rh(II)-prolinate catalyzed enantioselective insertion of allylic carbenoids into Si—H bond

Scheme 29. Rh-catalyzed asymmetric insertion of allylic carbenoids into Si—H bond

Scheme 30. Asymmetric insertion of allylic carbenoids into Si—H bond

Scheme 31. Cu-catalyzed enantioselective 1,4- or 1,6-addition reaction with silylboranes

Scheme 32. Cu-catalyzed asymmetric 1,2-addition of alkenyl N-tert-butylsulfonylimines with silylboranes

Scheme 33. Cu-catalyzed asymmetric 1,4-addition of α,β-unsaturated sulfonyl ketimines with silylboranes

Scheme 34. Cu-catalyzed double silicon-addition of electron-deficient conjugated enynes with silylboranes

Scheme 35. Copper(I)-catalyzed asymmetric addition of α,β-unsaturated sulfones with silylboranes

Scheme 36. Pt-catalyzed silaboration with 1,3-cyclohexadiene with silylboranes

Scheme 37. Palladium-catalyzed asymmetric silaboration of allenes with silylboranes

Scheme 38. Ni-catalyzed asymmetric three-component coupling reaction of 1,3-dienes, aldehydes and silylboranes

Scheme 39. Iridium-catalyzed carbonyl (trimethylsilyl)allylation

Scheme 40. NHC-catalyzed formal [4＋2] annulation of enals with β-silyl enones

Scheme 41. Rh-catalyst asymmetric 1,4-addition of β-silyl α,β-unsaturated ketones

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手性烯丙基硅烷的催化对映选择性合成

Catalytic Enantioselective Preparation of Chiral Allylsilanes

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