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. Biaggi
Primo
;
M. Benaglia
Secondo
;
S. Rossi;R. Annunziata
Ultimo
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%.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/42236
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