TY - JOUR
T1 - Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols
AU - Caselli, Alessandro
AU - Giovenzana, Giovanni B.
AU - Palmisano, Giovanni
AU - Sisti, Massimo
AU - Pilati, Tullio
N1 - Funding Information:
Financial support from MURST and CNR is gratefully acknowledged. The authors are indebted to Mr. G. Celentano (Istituto di Chimica Organica ‘A. Marchesini’, Università degli Studi, Milan, Italy) for performing chiral HPLC analyses. One of the authors (M.S.) is thankful to Dipartimento di Chimica Organica e Industriale (Università degli Studi, Milan, Italy) for kind hospitality.
PY - 2003/6/6
Y1 - 2003/6/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0038060691&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(03)00221-0
DO - 10.1016/S0957-4166(03)00221-0
M3 - Article
SN - 0957-4166
VL - 14
SP - 1451
EP - 1454
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 11
ER -