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Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions

Reisman, Sarah E. and Doyle, Abigail G. and Jacobsen, Eric N. (2008) Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions. Journal of the American Chemical Society, 130 (23). pp. 7198-7199. ISSN 0002-7863. PMCID PMC2574628. doi:10.1021/ja801514m.

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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.

Item Type:Article
Related URLs:
URLURL TypeDescription Information CentralArticle
Reisman, Sarah E.0000-0001-8244-9300
Doyle, Abigail G.0000-0002-6641-0833
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.
Funding AgencyGrant Number
NSF Predoctoral FellowshipUNSPECIFIED
NIH Postdoctoral FellowshipUNSPECIFIED
Issue or Number:23
PubMed Central ID:PMC2574628
Record Number:CaltechAUTHORS:20170331-155430409
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Official Citation:Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions Sarah E. Reisman, Abigail G. Doyle, and Eric N. Jacobsen Journal of the American Chemical Society 2008 130 (23), 7198-7199 DOI: 10.1021/ja801514m
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75607
Deposited By: Tony Diaz
Deposited On:01 Apr 2017 04:47
Last Modified:15 Nov 2021 16:35

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