Despite the structural similarities between carbonyls and imines, only the stereoselectivity of nucleophilic additions to the former are well understood. The Felkin-Anh model provides a method of predicting the major product of an addition to a carbonyl, but while one might expect similar results with imines, recent research has demonstrated that to not be the case. By synthesizing enolizable N-tosylimines, subjecting them to different nucleophiles and reaction conditions, and pursuing stereochemical proofs of the resulting products, we seek to build a model that will allow for improved understanding of stereochemically controlled nucleophilic additions to enolizable N-tosylimines.<br/>

Expanding the Felkin-Anh model: A study of the stereoselectivity of imines

255th National Meeting (2018)

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