A Convenient and Scaleable Synthesis of 11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene and Its Enantiomers

Martin E. Fox; Arne Gerlach; Ian C. Lennon; Graham Meek; Céline Praquin

doi:10.1055/s-2005-918444

SHORTPAPER

A Convenient and Scaleable Synthesis of 11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene and Its Enantiomers

Martin E. Fox, Arne Gerlach, Ian C. Lennon*, Graham Meek, Céline Praquin
Dowpharma, Chirotech Technology Ltd, A Subsidiary of The Dow Chemical Company, Unit 321 Cambridge Science Park, Milton Road, Cambridge, CB4 0WG, UK
Fax: +44(1223)506701; e-Mail: ilennon@dow.com;

Abstract

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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 followed by 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.

Key words

asymmetric catalysis - resolution - Diels-Alder reaction - palladium - allylic alkylation

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References

1

Current address: Bayer Cropscience AG, Industriepark Höchst, D-65926, Frankfurt, Germany.

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