Abstract
The rational design of systems which are capable of accelerating and/or controlling the stereochemical outcome of the Diels-Alder cycloaddition reaction between a furan and a maleimide is presented. The origins of the acceleration and control of the cycloaddition reactions are traced by kinetic studies - allied to molecular mechanics calculations - to the formation of complexes in which the dienes and the dieneophiles are placed in the appropriate arrangements for reaction, and, more importantly, to the formation of intramolecular hydrogen bonds in the cycloadducts.
Original language | English (US) |
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Pages (from-to) | 11365-11384 |
Number of pages | 20 |
Journal | Tetrahedron |
Volume | 55 |
Issue number | 37 |
DOIs | |
State | Published - Sep 10 1999 |
Keywords
- Cycloaddition
- Furans
- Kinetics
- Molecular recognition
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry