Published November 13, 2012
| Supplemental Material + Published
Journal Article
Open
Catalytic asymmetric synthesis of highly substituted pyrrolizidines
Chicago
An error occurred while generating the citation.
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.
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.Attached Files
Published - c2sc21617e.pdf
Supplemental Material - c2sc21617e.txt
Supplemental Material - supp.pdf
Supplemental Material - supp_2.pdf
Files
supp.pdf
Additional details
- PMCID
- PMC3614418
- Eprint ID
- 36751
- Resolver ID
- CaltechAUTHORS:20130204-094241868
- NSF
- CHE-0639094
- National Defense Science and Engineering Graduate (NDSEG) Fellowship
- NSF Graduate Research Fellowship
- DGE-1144469
- NIH
- RGM097582A
- Caltech
- Created
-
2013-02-05Created from EPrint's datestamp field
- Updated
-
2021-11-09Created from EPrint's last_modified field