Published October 20, 2010
| Accepted Version + Supplemental Material
Journal Article
Open
Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction
- Creators
- Repka, Lindsay M.
- Ni, Jane
-
Reisman, Sarah E.
Abstract
(R)-BINOL•SnCl_4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.
Additional Information
© 2010 American Chemical Society. Received August 23, 2010. Publication Date (Web): September 27, 2010. Published In Issue October 20, 2010 We thank Dr. Scott Virgil for insightful discussions; Drs. Michael Day and Larry Henling for X-ray crystallographic structural determination; and Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE- 0639094, CHE-0541745). NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). Financial support from the California Institute of Technology and the Baxter Foundation is gratefully acknowledged. Supporting Information: Experimental details, characterization data, and NMR spectral charts. This material is available free of charge via the Internet at http://pubs.acs.org.Attached Files
Accepted Version - nihms241123.pdf
Supplemental Material - ja107328g_si_001.cif
Supplemental Material - ja107328g_si_002.cif
Supplemental Material - ja107328g_si_003.pdf
Supplemental Material - ja107328g_si_004.pdf
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Additional details
- PMCID
- PMC3222144
- Eprint ID
- 20719
- DOI
- 10.1021/ja107328g
- Resolver ID
- CaltechAUTHORS:20101108-140057935
- CHE-0639094
- NSF
- CHE-0541745
- NSF
- RR027690
- NIH
- Caltech
- Baxter Foundation
- Created
-
2010-11-16Created from EPrint's datestamp field
- Updated
-
2021-11-09Created from EPrint's last_modified field