Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5270617 | Tetrahedron Letters | 2010 | 4 Pages |
Abstract
Chiral 1-phosphonodienes bearing a bicyclic (R,R)-1,3,2-dioxaphospholane or a (R,R)-1,3,2-diazaphospholidine auxiliary are potent dienes for asymmetric hetero Diels-Alder reactions. Their reactivity towards model nitroso and azodicarboxylate dienophiles has been studied by means of theoretical chemistry at the B3LYP/6-31Gââ level. This model, taking solvent effects into account, allowed us to identify parameters governing the stereoselectivity of this reaction. Our study emphasizes a synergy effect when increasing the steric hindrance of substituents of both partners. This led us to predict high levels of diastereoselectivity for one diene. Accordingly, we have hereby illustrated a convenient and original synthesis of this diene and its cycloadditions with commercially available nitroso and azodicarboxylate dienophiles.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jean-Christophe Monbaliu, Bernard Tinant, Daniel Peeters, Jacqueline Marchand-Brynaert,