Brochu, Michael P. and Brown, Sean P. and MacMillan, David W. C. (2004) Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes. Journal of the American Chemical Society, 126 (13). pp. 4108-4109. ISSN 0002-7863. doi:10.1021/ja049562z. https://resolver.caltech.edu/CaltechAUTHORS:20170420-115316089
![]() |
PDF
- Supplemental Material
See Usage Policy. 133kB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170420-115316089
Abstract
The first direct enantioselective catalytic α-chlorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective chlorination of aldehydes to generate α-chloro aldehydes, an important chiral synthon for chemical and medicinal agent synthesis. The use of imidazolidinone 3 as the asymmetric catalyst has been found to mediate the halogenation of a large variety of aldehyde substrates with the perchlorinated quinone 1 serving as the electrophilic chlorinating reagent. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. The capacity of catalyst 3 to override the inherent bias of resident stereogenicity in the chlorination of enantiopure β-chiral aldehydes is also described. Catalyst quantities of 5 mol % were generally employed in this study.
Item Type: | Article | ||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Related URLs: |
| ||||||||||||
Additional Information: | © 2004 American Chemical Society. Received 25 January 2004. Published online 11 March 2004. Published in print 1 April 2004. Financial support was provided by kind gifts from Bristol-Myers Squibb, Eli Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. Teresa Beeson is thanked for additional enantioselectivity analysis. | ||||||||||||
Funders: |
| ||||||||||||
Issue or Number: | 13 | ||||||||||||
DOI: | 10.1021/ja049562z | ||||||||||||
Record Number: | CaltechAUTHORS:20170420-115316089 | ||||||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170420-115316089 | ||||||||||||
Official Citation: | Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes Michael P. Brochu, Sean P. Brown, and David W. C. MacMillan Journal of the American Chemical Society 2004 126 (13), 4108-4109 DOI: 10.1021/ja049562z | ||||||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
ID Code: | 76770 | ||||||||||||
Collection: | CaltechAUTHORS | ||||||||||||
Deposited By: | Ruth Sustaita | ||||||||||||
Deposited On: | 21 Apr 2017 13:53 | ||||||||||||
Last Modified: | 15 Nov 2021 17:02 |
Repository Staff Only: item control page