Asymmetric diels-alder reaction. Cooperative blocking effect in organic synthesis

✍ Scribed by Kyoji Furuta; Kiyoshi Iwanaga; Hisashi Yamamoto

• Book ID: 104219071
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 237 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84991-6

✦ Synopsis

Remarkably high diastereoselectivity is observed in the organoaluminum catalyzed asymmetric Diels-Alder reaction of (-)-dimenthyl fumarate. The title reaction, pioneered by Walborsky' and thoroughly developed by Helmchen and Oppolzer, has been established as one of the most important tools in modern asymmetric synthesis. 2 In their study of the influence of concaveconvex topological features on asymmetric Diels-Alder reaction, they developed a number of facinating chiral auxiliary groups that in certain cases achieved levels of diastereoface differentiation significantly superior to those realized with simple menthol. Unfortunately, however, many of those methods Lf 1961, 26, 4778.