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American Chemical Society, Journal of Organic Chemistry, 3(75), p. 762-766, 2009

DOI: 10.1021/jo902283a

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Steric Control of α- and β-Alkylation of Azulenone Intermediates in a Guanacastepene A Synthesis

Journal article published in 2010 by Hao Wang, Karol Michalak, Michał Michalak, Gonzalo Jiménez-Osés ORCID, J. Wicha, K. N. Houk
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The origins of different stereoselectivities observed experimentally in the alkylations of azulenone precursors in the guanacastepene A synthesis have been determined through density functional theory investigations. The optimized transition structures of methylation of two different guanacastepene A precursors show that steric effects, rather than torsional factors that often determine such stereoselectivities, dictate the preferred products observed.