Palladium-catalyzed asymmetric allylic alkylations of colby pro-enolates with MBH carbonates : enantioselective access to quaternary C-F oxindoles
Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN 2 reaction catalyzed by Pd/...
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| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/139358 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN 2 reaction catalyzed by Pd/Ding-SKP-type ligands, and that occurs between Colby pro-enolates with MBH carbonates to afford the corresponding products featuring two consecutive stereogenic carbons, including a C-F quaternary stereogenic center. The reactions readily occur at ambient temperatures with high chemical yields and in excellent chemo-, diastereo- and enantioselective manners. This practically attractive stereochemical outcome, coupled with the operational simplicity and structural generality, bodes well for the synthetic application of this process in the preparation of a novel class of biologically relevant fluorine-containing compounds. |
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