Journal ArticleDOI
Application of pericyclic reactions to the synthesis of strained molecules. Intramolecular Diels-Alder cycloadditions. The synthesis of a (Z,Z)-bicyclo[4.3.1]deca-1,6-diene
K. J. Shea,L. D. Burke +1 more
Reads0
Chats0
About:
This article is published in Journal of Organic Chemistry.The article was published on 1985-03-01. It has received 12 citations till now. The article focuses on the topics: Pericyclic reaction & Diels–Alder reaction.read more
Citations
More filters
Journal ArticleDOI
The Type 2 Intramolecular Diels–Alder Reaction: Synthesis and Chemistry of Bridgehead Alkenes
TL;DR: The type 2 intramolecular Diels-Alder reaction and the resulting anti-Bredt alkenes have found application in organic synthesis and are verified in recent applications of the type 2 IMDA reaction as a key step in the total synthesis of complex natural products.
Journal ArticleDOI
Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide.
TL;DR: The T2IMDA provides a synthesis for rigid bridged bicyclic molecules that can be stereoselectively elaborated before ozonolysis of the bridgehead double bond and is amenable to the synthesis of terpene natural products.
Journal ArticleDOI
Intramolekulare Diels‐Alder‐Reaktion vom Typ 2: Synthese und Chemie von Brückenkopf‐Alkenen
TL;DR: The anti-Bredt-alkene, a bicyclische Molekule with a Bruckenkopf-Doppelbindung, galten lange als chemische Kuriositat.
Journal ArticleDOI
Disposable tethers in type 2 intramolecular diels-alder cycloaddition reactions. Applications in stereochemical control
TL;DR: Temporary union of diene and dienophile in the type 2 intramolecular Diels-Alder cycloaddition provides a general strategy for controlling both regio- and stereochemistry of the cycloadding as mentioned in this paper.
Journal ArticleDOI
Reversal of regiospecificity in the kinetic vs. thermodynamic enolization of bicyclic ketones. Direct bridgehead functionalization of the bicyclo[5.3.1]undecane ring system
Kenneth J. Shea,S. T. Sakata +1 more
TL;DR: In contrast to aliphatic ketones, deprotonation of bicyclo [5.3.1] undecenone 3 gives the more highly substituted bridgehead enolate under conditions of kinetic control while the less highly substituted enolate is formed under condition of thermodynamic control as mentioned in this paper.