Highly Diastereoselective Simmons-Smith Cyclopropanation of Allylic Amines

Article abstract of DOI:10.1021/ol035713b

(Equation presented) Cyclopropanation of allylic tertiary amines using the Simmons-Smith reagent has been achieved by employing chelating groups in close proximity to the amine. The chelating groups promote cyclopropanation at the expense of N-ylide formation. Using pseudoephedrine as the chelating group, high diastereoselectivity is observed.