Repka, Lindsay M. and Ni, Jane and Reisman, Sarah E. (2010) Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction. Journal of the American Chemical Society, 132 (41). pp. 14418-14420. ISSN 0002-7863 http://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935
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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.
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| 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. | ||||||||||||
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| Record Number: | CaltechAUTHORS:20101108-140057935 | ||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935 | ||||||||||||
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| Official Citation: | Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction Lindsay M. Repka, Jane Ni, Sarah E. Reisman Journal of the American Chemical Society 2010 132 (41), 14418-14420 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 20719 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||
| Deposited On: | 16 Nov 2010 20:10 | ||||||||||||
| Last Modified: | 26 Dec 2012 12:36 |
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