Kyoung Hoon Kim, Se-Il Lee, D. Lee
Sep 5, 2005
Citations
0
Influential Citations
43
Citations
Journal
Tetrahedron Letters
Abstract
Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels–Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Bronsted acid for the cycloaddition in a wet solvent.