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Synthesis 2019; 51(10): 2221-2229
DOI: 10.1055/s-0037-1610697
DOI: 10.1055/s-0037-1610697
paper
Further Structural Modification of Sulfur-Stabilized Silicon Cations with Binaphthyl Backbones
This research was supported by the Deutsche Forschungsgemeinschaft (Grant No. Oe 249/12-1).Further Information
Publication History
Received: 24 January 2019
Accepted: 29 January 2019
Publication Date:
11 March 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/201910/lookinside/thumbnails/ss-2019-z0048-op_10-1055_s-0037-1610697-1.jpg)
Abstract
The synthesis and spectroscopic characterization of two novel cationic silicon–sulfur Lewis pairs with a chiral 4,4′-disubstituted binaphthyl silepine backbone are described. Both Lewis acids induce significant enantioselectivity in the model Diels–Alder reaction of cyclohexa-1,3-diene and chalcone but additional substitution of the binaphthyl backbone exerts a minimal effect on enantioinduction compared to previously reported Lewis acids. Another silicon cation with a chiral spirocyclic backbone induces enantioselectivity in the same range but its synthesis is laborious.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610697.
- Supporting Information
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Cyclohexa-1,3-diene Diels–Alder reactions catalyzed by stabilized silicon cations:
For other enantioselective Diels–Alder reactions catalyzed by chiral silicon Lewis acids, see, for example:
Enantioselective cyclohexa-1,3-diene Diels–Alder reactions catalyzed by sulfur-stabilized silicon cations:
For chiral ligands containing a 1,1′-spirobiindane backbone for asymmetric catalysis, see: