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 a,b-unsaturated aldehydes with good exo stereoselectivity and enantioselectivities up to 71%.
Synthesis of new chiral cyclic 1,2-diamines and their evaluation as catalysts for enantioselective Diels-Alder reactions / C. Biaggi, M. Benaglia, S. Rossi, S. Proto, R. Annunziata. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 48:48(2007), pp. 8521-8525.
Synthesis of new chiral cyclic 1,2-diamines and their evaluation as catalysts for enantioselective Diels-Alder reactions
C. BiaggiPrimo
;M. BenagliaSecondo
;S. Rossi;R. AnnunziataUltimo
2007
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 a,b-unsaturated aldehydes with good exo stereoselectivity and enantioselectivities up to 71%.Pubblicazioni consigliate
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