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Synthesis 2024; 56(24): 3879-3888
DOI: 10.1055/a-2443-5162
DOI: 10.1055/a-2443-5162
paper
Enantioselective Synthesis of Axially Chiral Silacyclohexylidene Oxime Ethers by Chiral Phosphoric Acid Catalysis
This work was financially supported by the National Natural Science Foundation of China (Nos. 22471073, 22171087), Technology Innovation Project of Shanghai Municipal Agricultural Commission [No. HNK(T2023302)], Natural Science Foundation of Liaoning Province (No. 2022-KF-25-02), Innovation Program of Shanghai Municipal Education Commission (No. 2023ZKZD37), Ministry of Education of the People’s Republic of China (PCSIRT), and Fundamental Research Funds for the Central Universities.
Abstract
The first asymmetric condensation of prochiral silacyclohexanones with hydroxylamines by chiral phosphoric acid catalysis has been developed, which provides a facile and straightforward protocol for the enantioselective construction of valuable axially chiral silacyclohexylidene oxime ethers that are otherwise inaccessible. Notably, this constitutes a rare example for accessing silacycles featuring axial chirality.
Key words
axial chirality - chiral phosphoric acids - silacyclohexanones - enantioselective condensationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2443-5162.
- Supporting Information
Publication History
Received: 02 September 2024
Accepted after revision: 17 October 2024
Accepted Manuscript online:
17 October 2024
Article published online:
11 November 2024
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For selected reviews, see:
For selected examples of the synthesis of axially chiral spirosilanes, see:
For recent reviews, see:
Also see a leading review regarding catalytic desymmetrization: