Enantioselective Organocatalytic α-Fluorination of Aldehydes
- Creators
- Beeson, Teresa D.
- MacMillan, David W. C.
Abstract
The first direct enantioselective catalytic α-fluorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective fluorination of aldehydes to generate α-fluoro aldehydes, an important chiral synthon for medicinal agent synthesis. The use of imidazolidinone 1 as the asymmetric catalyst has been found to mediate the fluorination of a large variety of aldehyde substrates with N-fluorobenzenesulfonimide serving as the electrophilic source of fluorine. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 20 mol % were generally employed in this study, successful halogenation can be accomplished using catalyst loadings as low as 2.5 mol %.
Additional Information
© 2005 American Chemical Society. Received March 21, 2005. Publication Date (Web): May 19, 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. Mike Brochu is thanked for experimental efforts.Attached Files
Supplemental Material - ja051805fsi20050421_051112.pdf
Files
Name | Size | Download all |
---|---|---|
md5:7f6f3cdca95590619e191f7952465377
|
170.3 kB | Preview Download |
Additional details
- Eprint ID
- 77416
- DOI
- 10.1021/ja051805f
- Resolver ID
- CaltechAUTHORS:20170512-125249442
- NIH
- R01 GM66142-01
- Amgen
- Merck
- Created
-
2017-05-12Created from EPrint's datestamp field
- Updated
-
2021-11-15Created from EPrint's last_modified field