doi:10.1080/00958972.2012.674113">
 

Title

A density functional study of the relative stability of intermediates in a McMurry coupling reaction

Document Type

Article

Publication Date

2012

Department/School

Chemistry

Abstract

The intramolecular McMurry reaction is a relatively common method for assembling carbocycles in organic synthesis. Most typically, this reaction involves a reductive coupling mediated by Ti(II). However, there are few examples of intramolecular McMurry reactions in the presence of Lewis basic heteroatoms. In this work, we investigate the titanium-mediated McMurry coupling leading to a pyrrolidine methoxy keto ester. Specifically, we compare the relative energies of all possible reaction intermediates at the B3LYP/6-31G level of theory. The most stable intermediate is found to be the one resulting from deoxygenation of the α-methoxy ketone. The McMurry product is not predicted to form.

Link to Published Version

doi:10.1080/00958972.2012.674113