Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published September 10, 2003 | Supplemental Material
Journal Article Open

The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes

Abstract

The first direct enantioselective catalytic α-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate α-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described.

Additional Information

© 2003 American Chemical Society. Received 6 July 2003. Published online 19 August 2003. Published in print 1 September 2003. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Bristol-Myers Squibb, Johnson and Johnson, Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. C.J.S. is grateful to the NIH for postdoctoral fellowship support (NIH-F32-CA-091635-01).

Attached Files

Supplemental Material - ja037096ssi20030802_025802.pdf

Files

ja037096ssi20030802_025802.pdf
Files (55.2 kB)
Name Size Download all
md5:eb4923ae3f7a6a157c41e6a55f12c356
55.2 kB Preview Download

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023