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Understanding the Origins of Remote Asymmetric Induction in the Boron Aldol Reactions of β-Alkoxy Methyl Ketones

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Unilever Centre for Molecular Science Informatics, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom
Cite this: Org. Lett. 2006, 8, 19, 4299–4302
Publication Date (Web):August 16, 2006
https://doi.org/10.1021/ol061671q
Copyright © 2006 American Chemical Society

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    Abstract

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    We report theoretical studies into the remote 1,5-stereoinduction shown by certain types of β-alkoxy methyl ketones in boron-mediated aldol reactions with achiral aldehydes. For a range of common alkoxy groups, our calculations are in excellent agreement with experimentally observed diastereoselectivities. In the aldol transition structures, a stabilizing hydrogen bond between the alkoxy oxygen and formyl proton leads to preferential formation of the 1,5-adduct, by minimizing steric interactions between the β-alkyl group and one of the ligands on boron.

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    Cartesian coordinates, absolute energies, and imaginary frequencies of all transition structures reported in the paper. This material is available free of charge via the Internet at http://pubs.acs.org.

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