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Synlett 2021; 32(16): 1575-1580
DOI: 10.1055/a-1503-7976
DOI: 10.1055/a-1503-7976
synpacts
Catalytic Enantioselective Synthesis of Silicon-Stereogenic Alkoxysilanes and Siloxanes
We are grateful for financial support from the National Natural Science Foundation of China (21901104), Shenzhen Science and Technology Innovation Committee (JCYJ20190809142809370), and Guangdong Provincial Key Laboratory of Catalysis (2020B121201002).
Abstract
A Rh-catalyzed enantioselective intermolecular dehydrogenative Si–O coupling of dihydrosilanes with alcohols and silanols is demonstrated. Rh(I) catalyst equipped with a Josiphos ligand enables the highly enantioselective alcoholysis process of dihydrosilanes, giving access to a variety of functionalized triorgano-substituted silicon-stereogenic alkoxysilanes and siloxanes in decent yields and ee, which significantly expand the chemical space of the silicon-centered chiral molecules. Utility of this methodology is illustrated by the construction of circularly polarized luminescence (CPL) active chiral alkoxysilane small organic molecules.
1 Introduction
2 Conditions Optimization
3 Substrate Scope
4 Application
5 Conclusions
6 Experimental Procedure
Key words
asymmetric catalysis - dehydrogenative Si−O coupling - silicon-stereogenic alkoxysilanes - silicon-stereogenic siloxanes - CPL-active silanesPublication History
Received: 14 April 2021
Accepted after revision: 10 May 2021
Accepted Manuscript online:
10 May 2021
Article published online:
07 June 2021
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