Subscribe to RSS
DOI: 10.1055/a-2322-0904
Enantioselective Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines
This work was supported by the Fukuoka Naohiko Memorial Foundation.


Abstract
Chiral guanidine-catalyzed desymmetrization of meso-indan-1,3-diols was achieved via enantioselective silylation by using chlorosilanes in good yields with high selectivity. The combination of chlorosilanes and catalysts was determined by the substituents at the C-2 position on the substrate. It was found that the fused phenyl ring on the substrate was essential for achieving high selectivity. The proposed method was found to be applicable to several types of substrates under optimized reaction conditions. Double silylative kinetic resolution with additive Horeau amplification was observed to establish high selectivity.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2322-0904.
- Supporting Information
Publication History
Received: 23 April 2024
Accepted after revision: 07 May 2024
Accepted Manuscript online:
07 May 2024
Article published online:
27 May 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany