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Issue 12, 2019
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Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

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Abstract

In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of α-alkoxy and α,β-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the α position and the stereoelectronic influence of the oxygen protecting groups at the α and β positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the β-substituent. The synergistic effect between the α,β-syn and α,β-anti-bisalkoxy stereocenters was elucidated. In the presence of the β-alkoxy center, the reaction proceeds through the Goodman–Paton 1,5-stereoinduction model, experiencing a minor influence of the α-alkoxy center.

Graphical abstract: Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

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Article information


Submitted
13 Feb 2019
Accepted
21 Feb 2019
First published
22 Feb 2019

Org. Biomol. Chem., 2019,17, 3167-3180
Article type
Paper

Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

A. A. G. Fernandes, I. A. Leonarczyk, M. A. B. Ferreira and L. C. Dias, Org. Biomol. Chem., 2019, 17, 3167 DOI: 10.1039/C9OB00358D

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