Diastereoselective Diels-Alder reactions of a novel cyclopropenyl-containing chiral auxiliary.
A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.
Henderson
Jeff R
JR
Department of Chemistry, University of Calgary, Calgary, AB, T2N 1N4, Canada.
Parvez
Masood
M
Keay
Brian A
BA