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 June 11, 2008 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions

Abstract

Asymmetric, catalytic reactions of oxocarbenium ions are reported. Simple, chiral urea and thiourea derivatives are shown to catalyze the enantioselective substitution of silyl ketene acetals onto 1-chloroisochromans. A mechanism involving anion binding by the chiral catalyst to generate a reactive oxocarbenium ion is invoked. Catalysts bearing tertiary benzylic amide groups afforded highest enantioselectivities, with the optimal structure being derived from enantioenriched 2-arylpyrrolidine derivatives.

Additional Information

© 2008 American Chemical Society. Received February 28, 2008; Publication Date (Web): May 14, 2008. This work was supported by the NIGMS (GM-43214), by predoctoral fellowship support to A.G.D. from the NSF, and postdoctoral fellowship to S.E.R. from the NIH. We thank Dr. Kevin Campos (Merck Process) for helpful discussions and generous donations of N-Boc-2-arylpyrrolidine derivatives.

Attached Files

Accepted Version - nihms-47783.pdf

Supplemental Material - ja801514m-file003.pdf

Files

ja801514m-file003.pdf
Files (1.3 MB)
Name Size Download all
md5:5ff49acdffa4c944975d692c2cd77741
1.2 MB Preview Download
md5:53b38d7f1b179d120b2773633a941d18
132.3 kB Preview Download

Additional details

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