𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Diastereoselective Diels–Alder Reaction of 5-(Indol-2-yl)-pyran-2-one

✍ Scribed by Daniele Passarella; Giordano Lesma; Marisa Martinelli; Alessandra Silvani; Margalida Cantò; Josè Hidalgo


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
89 KB
Volume
56
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis


AbstractÐ5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and electron-rich dienophiles. Lanthanide shift reagents have been shown to be ef®cient catalysts for the inverse electron demand Diels±Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of bicycloadducts with primary amines is described.


📜 SIMILAR VOLUMES


π-Facial diastereoselectivity in Diels-A
✍ Arvin M Naperstkow; John B Macaulay; Michael J Newlands; Alex G Fallis 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 289 KB

A series of [4 + 21 cycloadditions with 2,Sdimethylthiophene oxide (2), generated in situ by peracid oxidation of 2,Sdimethylthiophene (l), are described. In all cases the syn adduct (with respect to the sulfoxide oxygen) is formed exclusively. Recently the x-facial diastereoselectivity encountered

Asymmetric aza-Diels–Alder reactions of
✍ Jeffrey T Kuethe; Ian W Davies; Peter G Dormer; Robert A Reamer; David J Mathre; 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 111 KB

The aza-Diels-Alder reaction of substituted indole 2-carboxaldehydes with Danishefsky's diene has been investigated. The reaction proceeds with a high degree of diastereoselectivity providing highly functionalized 2-(2-piperidyl)indoles which are further elaborated into novel polycyclic heterocycles