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Synthesis 2023; 55(17): 2609-2638
DOI: 10.1055/s-0042-1751459
DOI: 10.1055/s-0042-1751459
review
Transition-Metal-Catalyzed Synthesis of α-Chiral Allylsilanes
R.P.S. thanks the École Doctorale ED406 for a Ph.D. grant.
Abstract
Over the past 30 years, the synthesis of α-chiral allylsilanes have attracted much interest. These compounds are indeed versatile building blocks and linchpins ranking among the most useful organic scaffolds due to the large number of transformations that both their C–Si bond and C–C double bond can undergo. They therefore occupy a unique place in the arsenal of the organic chemist, particularly for the synthesis of complex molecules. In this review, an overview of transition-metal-catalyzed syntheses of α-chiral allylsilanes is presented.
1 Introduction
2 Addition of Silylmetals
2.1 Silylation of Allylic Electrophiles
2.2 Conjugate Addition
2.3 1,2-Addition to N-tert-Butylsulfonyl Imines
2.4 Silaboration
3 Addition of Nucleophiles
3.1 Substitution of γ-Silylated Allylic Electrophiles
3.2 1,4-Conjugate Addition to β-Silyl Enones and Enoates
3.3 Reduction of γ-Silylated Allylic Carbonates
4 Hydrosilylation
4.1 1,4-Hydrosilylation of 1,3-Dienes
4.2 1,2-Hydrosilylation of 1,3-Dienes
4.3 1,2-Hydrosilylation of Allenes
5 Cross-Coupling Reactions
5.1 Cross-Coupling of Vinyl Halides
5.2 Retroallylation of δ-Silylated Homoallylic Alcohols
5.3 Multicomponent Cross-Coupling of 1,3-Dienes
6 Insertion Reactions
6.1 Vinylcarbenoid Insertion into Si–H Bonds
6.2 Silylene Insertion into Allylic C–O Bonds
7 Rearrangements
7.1 Intramolecular γ-Silylation of Allylic Disilanyl Ethers
7.2 Domino Isomerization–Claisen Rearrangement of γ-Silylated Bis(allylic) Ethers
8 Miscellaneous
9 Conclusion
Key words
allylsilanes - allylic substitution - conjugate addition - enantioselectivity - hydrosilylation - regioselectivityPublication History
Received: 28 March 2023
Accepted after revision: 26 April 2023
Article published online:
07 June 2023
© 2023. Thieme. All rights reserved
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