In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
Document Type
Article
Publication Date
10-1-2015
Abstract
The chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis-silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio- and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.
Publication Title
European Journal of Organic Chemistry
Volume
2015
Issue
30
First Page
6615
Last Page
6623
Digital Object Identifier (DOI)
10.1002/ejoc.201500853
ISSN
1434193X
E-ISSN
10990690
Citation Information
Borosky, & Laali, K. K. (2015). In Silico Study on Chemical Properties and Reactivity of Enal Derivatives. European Journal of Organic Chemistry, 2015(30), 6615–6623. https://doi.org/10.1002/ejoc.201500853