Highly diastereoselective Simmons-Smith cyclopropanation of allylic amines.
[reaction: see text] 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.
Aggarwal
Varinder K
VK
Department of Chemistry, University of Bristol, Cantock's Close, Bristol, U.K. v.aggarwal@bristol.ac.uk
Fang
Guang Yu
GY
Meek
Graham
G