The Lactone Concept: An Efficient Pathway to Axially Chiral Natural Products and Useful Reagents
- 1 April 1999
- journal article
- review article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1999 (04) , 525-558
- https://doi.org/10.1055/s-1999-3435
Abstract
A highly efficient concept for the stereoselective synthesis of axially chiral biaryl target molecules is presented: the atroposelective ring cleavage of configurationally unstable lactone-bridged biaryls. The method has almost no restrictions concerning the substitution pattern, works even for substrates with high steric hindrance at the ortho-position(s) of the axis, and allows the optional, atropo-divergent preparation of each atropisomer from the same biaryl lactone precursor and a recycling of the undesired minor product in the sense of a chiral economy. A brpad series of successful application in natural product and ligand syntheses underlines the high value of the method.Keywords
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