Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5287244 | Tetrahedron Letters | 2005 | 4 Pages |
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 Brønsted acid for the cycloaddition in a wet solvent.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Kyoung Hoon Kim, Seil Lee, Dae-Woong Lee, Dong-Hyun Ko, Deok-Chan Ha,