Advances in Organic Catalysis: The Design of a Novel Asymmetric, Organocatalytic Intramolecular Diels Alder Reaction

Author: Wilson, Rebecca Mary

Year: 2002

Degree: Master's thesis

Advisor: Unknown, Unknown

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/emr9-4m89

Abstract

[Introduction] The Diels-Aider reaction is one of the most powerful and widely exploited methods available for generating six-membered rings. Similarly, the intramolecular Diels-Alder (IMDA), in which the diene and dienophile reacting partners are tethered, has received a great deal of attention from synthetic chemists in recent years. The IMDA usually proceeds with excellent levels of regio- and stereocontrol to generate complex bicyclic systems with up to four contiguous stereocenters from relatively simple precursors. There have been a number of efforts to develop diastereoselective variants of the IMDA, but there are considerably fewer examples of catalytic, asymmetric IMDA variants.

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