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Enantioselective Synthesis of Chiral 3-Substituted-3-silylpropionic Esters via Rhodium/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
- Source :
- Advanced Synthesis & Catalysis. 359:2585-2589
- Publication Year :
- 2017
- Publisher :
- Wiley, 2017.
-
Abstract
- We successfully developed asymmetric hydrogenation of β-silyl-α,β-unsaturated esters to prepare chiral 3-substituted-3-silylpropionic ester products catalyzed by rhodium/bisphosphine-thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1 500 TON). Moreover, our hydrogenation product can be efficiently converted to other important organic molecules, such as chiral ethyl (R)-3-hydroxy-3-phenylpropanoate, (R)-3-(dimethyl(phenyl)silyl)-3-phenylpropanoic acid.
- Subjects :
- Silylation
010405 organic chemistry
Asymmetric hydrogenation
Enantioselective synthesis
chemistry.chemical_element
Noyori asymmetric hydrogenation
General Chemistry
010402 general chemistry
01 natural sciences
0104 chemical sciences
Rhodium
Catalysis
chemistry.chemical_compound
chemistry
Thiourea
Yield (chemistry)
Organic chemistry
Subjects
Details
- ISSN :
- 16154150
- Volume :
- 359
- Database :
- OpenAIRE
- Journal :
- Advanced Synthesis & Catalysis
- Accession number :
- edsair.doi...........33c8a5084dd6f3f299fa1f1564d467b0