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In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
Author(s) -
Borosky Gabriela L.,
Laali Kenneth K.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500853
Subject(s) - chemistry , electrophile , reactivity (psychology) , nucleophile , oxonium ion , stereoselectivity , substituent , steric effects , protonation , reagent , computational chemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , ion , alternative medicine , pathology
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.