Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols

Alessandro Caselli, Giovanni B. Giovenzana, Giovanni Palmisano, Massimo Sisti, Tullio Pilati

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

The new C2-symmetrical 1,2-diamine {N,N′-bis[(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-1,2- ethanediamine}3 has been synthesized from commercial (1R)-(+)-camphor 1 and scrutinized as ligand in the oxidative biaryl coupling of naphthol derivatives. Under the optimal conditions employing a Cu(I)-3 triflate complex (10 mol%) in dichloroethane-MeCN and molecular sieves with air as the oxidant, aryl coupling of naphthol derivatives could be achieved in satisfactory yields (48-90% yield) and ees of up to 65%. The ester moiety at the 3-position of the substrate was found to be crucial for a satisfactory asymmetric induction in the present coupling reaction.

Lingua originaleInglese
pagine (da-a)1451-1454
Numero di pagine4
RivistaTetrahedron Asymmetry
Volume14
Numero di pubblicazione11
DOI
Stato di pubblicazionePubblicato - 6 giu 2003

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