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Asymmetric Synthesis of Aminochromanes via Intramolecular Indium-Mediated Allylation of Chiral Hydrazones

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Department of Chemistry and Molecular Biology, North Dakota State University, Department 2735, P.O. Box 6050, Fargo, North Dakota 58108-6050
Cite this: J. Org. Chem. 2009, 74, 18, 7183–7186
Publication Date (Web):August 24, 2009
https://doi.org/10.1021/jo901195g
Copyright © 2009 American Chemical Society

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    Abstract

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    The asymmetric intramolecular indium-mediated cyclization reaction delivers chromanes with excellent diastereoselectivity (68−91% yield, dr >99:1). The reaction was efficient for aryl substrates with both electron-withdrawing and -donating groups. Carboxylic acid additives were found to be necessary for optimal reaction.

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    Experimental procedures, characterization data, and 1H and 13C NMR spectra for all new compounds. Crystallographic data for 3a. This material is available free of charge via the Internet at http://pubs.acs.org.

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