M. Fox, A. Gerlach, I. Lennon
Dec 1, 2005
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Influential Citations
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Journal
Synthesis
Abstract
A convenient synthesis of 11,12-diamino-9,10-dihydro-9,10-ethanoanthracene (1) is described. A Diels-Alder reaction between fumaryl chloride and anthracene provides an acid chloride. Conversion into an acyl azide followedby a thermal Curtius rearrangement and saponification affords the racemic diamine. Diastereoisomeric salt resolution provides the single enantiomer products, which are used as the chiral backbone of several ligands in asymmetric catalysis, including the Trost asymmetric allylic alkylation ligand 2.