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. https://resolver.caltech.edu/CaltechAUTHORS:20170331-155430409

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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.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja801514m	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja801514m	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja801514m	Publisher	Supporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2574628/	PubMed Central	Article

ORCID:

Author	ORCID
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.

Funders:

Funding Agency	Grant Number
NIH	GM-43214
NSF Predoctoral Fellowship	UNSPECIFIED
NIH Postdoctoral Fellowship	UNSPECIFIED

Issue or Number:

PubMed Central ID:

PMC2574628

DOI:

10.1021/ja801514m

Record Number:

CaltechAUTHORS:20170331-155430409

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170331-155430409

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

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ID Code:

75607

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

01 Apr 2017 04:47

Last Modified:

15 Nov 2021 16:35

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