Toward solutions to the problem of controlling E-O-enolate geometry in Ireland-Claisen rearrengements transition state

by Alwarsh, Sefat A.; McIntosh, Matt

Lactate ester enolates have been used by several groups as intermediates in the Ireland-Claisen rearrangement and other reactions. While Z-(OM)-lactate enolates can be generated with good to excellent stereoselectivity as a consequence of metal chelation, there are no reported methods for selectively generating the corresponding E-(OM)-lactate ester enolates. We will describe our studies directed toward generating E-lactate enolates using Zakarian's recently reported double diastereoselectivity approach.