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Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution

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Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6, and Chemical Development and Catalysis Department, Solvias AG, WRO-1055.6.62, P.O. Box, 4002 Basel, Switzerland
†University of Toronto.
‡Solvias AG.
Cite this: Org. Lett. 2010, 12, 23, 5418–5421
Publication Date (Web):November 2, 2010
https://doi.org/10.1021/ol1022239
Copyright © 2010 American Chemical Society

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    Abstract

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    Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.

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    Experimental procedures, characterization data for new compounds, and additional data tables. This material is available free of charge via the Internet at http://pubs.acs.org.

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