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Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation

Kunz, Roxanne K. and MacMillan, David W. C. (2005) Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation. Journal of the American Chemical Society, 127 (10). pp. 3240-3241. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170420-063814113

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Abstract

A new method for enantioselective organocatalytic cyclopropanation is described. This study outlines the identification of a new class of iminium catalyst based on the concept of directed electrostatic activation (DEA). This novel organocatalytic mechanism exploits dual activation of ylide and enal substrates through a proposed electrostatic activation and stereodirected protocol. Formation of trisubstituted cyclopropanes with high levels of enantio- and diastereoinduction is accomplished for a variety of α,β-unsaturated aldehydes and sulfonium ylides. In addition, mechanistic studies have found that this cyclopropanation reaction exhibits enantioselectivity and reactivity profiles that are in accord with the proposed DEA step.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja042774bDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja042774bPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja042774bPublisherSupporting Information
Additional Information:© 2005 American Chemical Society. Received 1 December 2004. Published online 18 February 2005. Published in print 1 March 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. R.K.K. is grateful for an NIH postdoctoral fellowship (5 F32 GM 066595-02).
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
NIH Postdoctoral Fellowship5 F32 GM 066595-02
Issue or Number:10
Record Number:CaltechAUTHORS:20170420-063814113
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170420-063814113
Official Citation:Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation Roxanne K. Kunz and David W. C. MacMillan Journal of the American Chemical Society 2005 127 (10), 3240-3241 DOI: 10.1021/ja042774b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76740
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Apr 2017 14:58
Last Modified:03 Oct 2019 17:49

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