Synthesis of new chiral cyclic 1,2-diamines and their evaluation as catalysts for enantioselective Diels-Alder reactions |
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Authors: | Cinzia Biaggi Sergio Rossi Stefano Proto Rita Annunziata |
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Affiliation: | Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy |
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Abstract: | The synthesis of new, enantiomerically pure cyclic 1,2-diamine structures was realized through a zinc promoted coupling of chiral bis-imines easily prepared starting from a chiral biphenyl dicarboxylic acid. The catalytic properties of such novel compounds were preliminarily studied; the trifluoroacetate salts of these chiral 1,2-diamines were shown to be able to catalyze the Diels-Alder reaction between cyclopentadiene and α,β-unsaturated aldehydes with good exo stereoselectivity and enantioselectivities up to 71%. |
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