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Enantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D

Wilson, Rebecca M. and Jen, Wendy S. and MacMillan, David W. C. (2005) Enantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D. Journal of the American Chemical Society, 127 (33). pp. 11616-11617. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170420-133643860

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Abstract

The first direct enantioselective organocatalytic intramolecular Diels−Alder reaction has been accomplished. The use of iminium catalysis has provided a new catalytic strategy for the enantioselective [4 + 2] cycloisomerization of a wide variety of tethered diene-enal systems. The use of imidazolidinones 1 and 2 as the asymmetric catalysts has been found to mediate the enantioselective construction of [4.4.0] and [4.3.0] ring systems. Application of this methodology to the highly efficient asymmetric synthesis of the marine metabolite solanpyrone D has also been accomplished. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. Importantly, this technology has been utilized to execute the first enantioselective, catalytic Type II IMDA reaction.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja054008qDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja054008qPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja054008qPublisherSupporting Information
Additional Information:© 2005 American Chemical Society. Received June 16, 2005. Publication Date (Web): July 28, 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen, Merck, and Astellas USA Foundation. W.S.J. and R.M.W. are grateful for NSF Predoctoral Fellowships.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
Astellas USA FoundationUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:33
Record Number:CaltechAUTHORS:20170420-133643860
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170420-133643860
Official Citation:Enantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D Rebecca M. Wilson, Wendy S. Jen, and David W. C. MacMillan Journal of the American Chemical Society 2005 127 (33), 11616-11617 DOI: 10.1021/ja054008q
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76782
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:20 Apr 2017 20:44
Last Modified:03 Oct 2019 17:49

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