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Catalytic asymmetric synthesis of highly substituted pyrrolizidines

Lim, Andrew D. and Codelli, Julian A. and Reisman, Sarah E. (2012) Catalytic asymmetric synthesis of highly substituted pyrrolizidines. Chemical Science, 4 (2). pp. 650-654. ISSN 2041-6520. PMCID PMC3614418. doi:10.1039/c2sc21617e. https://resolver.caltech.edu/CaltechAUTHORS:20130204-094241868

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Abstract

A catalytic asymmetric double (1,3)-dipolar cycloaddition reaction has been developed. Using a chiral silver catalyst, enantioenriched pyrrolizidines can be prepared in one flask from inexpensive, commercially available starting materials. The pyrrolizidine products contain a variety of substitution patterns and as many as six stereogenic centers.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c2sc21617e DOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2013/SC/c2sc21617ePublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3614418/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2013 The Royal Society of Chemistry. Received 28th September 2012. Accepted 31st October 2012. First published on the web 13 Nov 2012. We thank the late Dr Michael Day and Mr Larry Henling for X-ray crystallographic structure determination, Dr David vander Velde for assistance with NMR structure determination, as well as Prof. Brian Stoltz, Dr Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Dr Jacob Cha and Dr. Scott Virgil are acknowledged for assistance with QUINAP preparation. We also thank Sigma- Aldrich for a kind donation of chemicals. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the National Science Foundation (NSF) CRIF program (CHE-0639094). Fellowship support was provided by the Department of Defense (DoD) through the National Defense Science & Engineering Graduate Fellowship Program (J. A. C.), and by the NSF Graduate Research Fellowship Program (J. A. C. and A. D. L., Grant no. DGE- 1144469). S. E. R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology and the NIH (NIGMS RGM097582A) is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSFCHE-0639094
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
NSF Graduate Research FellowshipDGE-1144469
NIHRGM097582A
CaltechUNSPECIFIED
Issue or Number:2
PubMed Central ID:PMC3614418
DOI:10.1039/c2sc21617e
Record Number:CaltechAUTHORS:20130204-094241868
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130204-094241868
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:36751
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Feb 2013 23:17
Last Modified:09 Nov 2021 23:24

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