Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols
The first asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates has been developed. The opposite enantiomers of adducts, containing a trifluoromethylated hetero-quaternary stereogenic centers, could be obtained by utilizing two pseudo-enantiomeric Cinch...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2014
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/100993 http://hdl.handle.net/10220/19696 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | The first asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates has been developed. The opposite enantiomers of adducts, containing a trifluoromethylated hetero-quaternary stereogenic centers, could be obtained by utilizing two pseudo-enantiomeric Cinchona alkaloid-derived tertiary amine/squaramides as catalysts. Potassium dihydrogen phosphate was found to accelerate the reaction rate without compromising the enantioselective excess. A variety of chiral trifluoromethylated tertiary thioethers and thiols were readily prepared with excellent enantioselectivity. |
|---|