@ARTICLE{Caselli20031451,
author={Caselli, A. and Giovenzana, G.B. and Palmisano, G. and Sisti, M. and Pilati, T.},
title={Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols},
journal={Tetrahedron Asymmetry},
year={2003},
volume={14},
number={11},
pages={1451-1454},
doi={10.1016/S0957-4166(03)00221-0},
note={cited By 29},
url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038060691&doi=10.1016%2fS0957-4166%2803%2900221-0&partnerID=40&md5=54c675f7ed410a92343e34f1502a144b},
affiliation={Dipto. di Chim. Organ. e Industriale, Univ. degli Studi di Milano, Via Venezian 21, I-20133 Milano, Italy; Dipto. Sci. Chimiche Alimentari F., Univ. Piemonte Orientale 'A. A.', Via Bovio 6, I-28100 Novara, Italy; Dipto. Sci. Chimiche Fisiche M., Univ. degli Studi dell'Insubria, Via Valleggio 11, I-2210 Como, Italy; CNR-Ist. Sci. Tecnologie Molecolari, Via Golgi 19, I-20133 Milano, Italy},
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. © 2003 Elsevier Science Ltd. All rights reserved.},
keywords={1,2 diamine [n,n' bis[1,7,7 trimethylbicyclo[2.2.1]hept 2 yl] 1,2 ethanediamine];  camphor;  diamine;  ester derivative;  ligand;  naphthol derivative;  polycyclic aromatic hydrocarbon derivative;  trifluoromethanesulfonic acid;  unclassified drug, article;  asymmetric synthesis;  carbon nuclear magnetic resonance;  crystal structure;  drug synthesis;  high performance liquid chromatography;  oxidation;  priority journal},
chemicals_cas={camphor, 464-49-3, 76-22-2, 8008-51-3; trifluoromethanesulfonic acid, 1493-13-6},
references={Lucet, D., Le Gall, T., Mioskowski, C., (1998) Angew. Chem., Int. Ed. Engl., 37, p. 2580; Whitesell, J.K., (1989) Chem. Rev., 89, p. 1581; Togni, A., Venanzi, L.M., (1994) Angew. Chem., Int. Ed. Engl., 33, p. 497; Tomioka, K., (1990) Synthesis, p. 541; Bennani, Y.L., Hanessian, S., (1997) Chem. Rev., 97, p. 3161; Nantz, M.H., Lee, D.A., Bender, D.M., Roohi, A.H., (1992) J. Org. Chem., 57, p. 6653; Kotsuki, H., Kuzume, H., Gohda, T., Fukuhara, M., Ochi, M., Oishi, T., Hirama, M., Shiro, M., (1995) Tetrahedron: Asymmetry, 6, p. 2227; Giovenzana, G.B., Pagliarin, R., Palmisano, G., Pilati, T., Sisti, M., (1999) Tetrahedron: Asymmetry, 10, p. 4277; Cabella, G., Jommi, G., Pagliarin, R., Sello, G., Sisti, M., (1995) Tetrahedron, 51, p. 1817; Raza, Z., Dakovic, S., Vinkovic, V., Šunjic, V., (1996) Croat. Chem. Acta, 69, p. 1545. , These authors reacted (1R)-camphor and ethylenediamine in toluene and in the presence of p-toluenesulfonic acid and obtained the diimine 2 in 61% yield; Jian, L.S., Aigiao, M., Guishu, Y., Yaozhong, J., (1992) Synth. Commun., 22, p. 1497; Periasamy, M., Devasagayaraj, A., Satyanarayana, N., Narayana, C., (1989) Synth. Commun., 19, p. 565; Ipaktschi, J., (1984) Chem. Ber., 117, p. 856; note; note; note; Rosini, C., Franzini, L., Raffaeli, A., Salvatori, P., (1992) Synthesis, p. 502; Nakajima, M., Miyoshi, I., Kanayama, K., Hashimoto, S., Noji, M., Koga, K., (1999) J. Org. Chem., 64, p. 2264. , and references cited therein; Smrčina, M., Poláková, J., Vyskočil, Š., Kočovský, P., (1993) J. Org. Chem., 58, p. 4534; Kozlowski, M.C., Li, X., Carrol, P.J., Xu, Z., (2002) Organometallics, 21, p. 4513; Li, X., Yang, J., Kozlowski, M.C., (2001) Org. Lett., 3, p. 1137; Hovorka, M., Ščigel, R., Gunterová, J., Tichý, M., Závada, J., (1992) Tetrahedron, 48, p. 9503; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G., Camalli, G., (1994) J. Appl. Crystallogr., 27, p. 435; Sheldrick, G.M., (1997) SHELX-97. Program for the Refinement of Crystal Structures, , University of Göttingen, Germany},
correspondence_address1={Palmisano, G.; Dipto. Sci. Chimiche Fisiche M., Via Valleggio 11, I-2210 Como, Italy; email: giovanni.palmisano@uninsubria.it},
publisher={Elsevier Ltd},
issn={09574166},
coden={TASYE},
language={English},
abbrev_source_title={Tetrahedron Asymmetry},
document_type={Article},
source={Scopus},
}

{"_id":"eb7cJRrnhBPyK8KNA","bibbaseid":"caselli-giovenzana-palmisano-sisti-pilati-synthesisofc2symmetricaldiaminebasedon1rcamphorandapplicationtooxidativearylcouplingofnaphthols-2003","author_short":["Caselli, A.","Giovenzana, G.","Palmisano, G.","Sisti, M.","Pilati, T."],"bibdata":{"bibtype":"article","type":"article","author":[{"propositions":[],"lastnames":["Caselli"],"firstnames":["A."],"suffixes":[]},{"propositions":[],"lastnames":["Giovenzana"],"firstnames":["G.B."],"suffixes":[]},{"propositions":[],"lastnames":["Palmisano"],"firstnames":["G."],"suffixes":[]},{"propositions":[],"lastnames":["Sisti"],"firstnames":["M."],"suffixes":[]},{"propositions":[],"lastnames":["Pilati"],"firstnames":["T."],"suffixes":[]}],"title":"Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols","journal":"Tetrahedron Asymmetry","year":"2003","volume":"14","number":"11","pages":"1451-1454","doi":"10.1016/S0957-4166(03)00221-0","note":"cited By 29","url":"https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038060691&doi=10.1016%2fS0957-4166%2803%2900221-0&partnerID=40&md5=54c675f7ed410a92343e34f1502a144b","affiliation":"Dipto. di Chim. Organ. e Industriale, Univ. degli Studi di Milano, Via Venezian 21, I-20133 Milano, Italy; Dipto. Sci. Chimiche Alimentari F., Univ. Piemonte Orientale 'A. A.', Via Bovio 6, I-28100 Novara, Italy; Dipto. Sci. Chimiche Fisiche M., Univ. degli Studi dell'Insubria, Via Valleggio 11, I-2210 Como, Italy; CNR-Ist. Sci. Tecnologie Molecolari, Via Golgi 19, I-20133 Milano, Italy","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- ethanediamine3 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. © 2003 Elsevier Science Ltd. All rights reserved.","keywords":"1,2 diamine [n,n' bis[1,7,7 trimethylbicyclo[2.2.1]hept 2 yl] 1,2 ethanediamine]; camphor; diamine; ester derivative; ligand; naphthol derivative; polycyclic aromatic hydrocarbon derivative; trifluoromethanesulfonic acid; unclassified drug, article; asymmetric synthesis; carbon nuclear magnetic resonance; crystal structure; drug synthesis; high performance liquid chromatography; oxidation; priority journal","chemicals_cas":"camphor, 464-49-3, 76-22-2, 8008-51-3; trifluoromethanesulfonic acid, 1493-13-6","references":"Lucet, D., Le Gall, T., Mioskowski, C., (1998) Angew. Chem., Int. Ed. Engl., 37, p. 2580; Whitesell, J.K., (1989) Chem. Rev., 89, p. 1581; Togni, A., Venanzi, L.M., (1994) Angew. Chem., Int. Ed. Engl., 33, p. 497; Tomioka, K., (1990) Synthesis, p. 541; Bennani, Y.L., Hanessian, S., (1997) Chem. Rev., 97, p. 3161; Nantz, M.H., Lee, D.A., Bender, D.M., Roohi, A.H., (1992) J. Org. Chem., 57, p. 6653; Kotsuki, H., Kuzume, H., Gohda, T., Fukuhara, M., Ochi, M., Oishi, T., Hirama, M., Shiro, M., (1995) Tetrahedron: Asymmetry, 6, p. 2227; Giovenzana, G.B., Pagliarin, R., Palmisano, G., Pilati, T., Sisti, M., (1999) Tetrahedron: Asymmetry, 10, p. 4277; Cabella, G., Jommi, G., Pagliarin, R., Sello, G., Sisti, M., (1995) Tetrahedron, 51, p. 1817; Raza, Z., Dakovic, S., Vinkovic, V., Šunjic, V., (1996) Croat. Chem. Acta, 69, p. 1545. , These authors reacted (1R)-camphor and ethylenediamine in toluene and in the presence of p-toluenesulfonic acid and obtained the diimine 2 in 61% yield; Jian, L.S., Aigiao, M., Guishu, Y., Yaozhong, J., (1992) Synth. Commun., 22, p. 1497; Periasamy, M., Devasagayaraj, A., Satyanarayana, N., Narayana, C., (1989) Synth. Commun., 19, p. 565; Ipaktschi, J., (1984) Chem. Ber., 117, p. 856; note; note; note; Rosini, C., Franzini, L., Raffaeli, A., Salvatori, P., (1992) Synthesis, p. 502; Nakajima, M., Miyoshi, I., Kanayama, K., Hashimoto, S., Noji, M., Koga, K., (1999) J. Org. Chem., 64, p. 2264. , and references cited therein; Smrčina, M., Poláková, J., Vyskočil, Š., Kočovský, P., (1993) J. Org. Chem., 58, p. 4534; Kozlowski, M.C., Li, X., Carrol, P.J., Xu, Z., (2002) Organometallics, 21, p. 4513; Li, X., Yang, J., Kozlowski, M.C., (2001) Org. Lett., 3, p. 1137; Hovorka, M., Ščigel, R., Gunterová, J., Tichý, M., Závada, J., (1992) Tetrahedron, 48, p. 9503; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G., Camalli, G., (1994) J. Appl. Crystallogr., 27, p. 435; Sheldrick, G.M., (1997) SHELX-97. Program for the Refinement of Crystal Structures, , University of Göttingen, Germany","correspondence_address1":"Palmisano, G.; Dipto. Sci. Chimiche Fisiche M., Via Valleggio 11, I-2210 Como, Italy; email: giovanni.palmisano@uninsubria.it","publisher":"Elsevier Ltd","issn":"09574166","coden":"TASYE","language":"English","abbrev_source_title":"Tetrahedron Asymmetry","document_type":"Article","source":"Scopus","bibtex":"@ARTICLE{Caselli20031451,\nauthor={Caselli, A. and Giovenzana, G.B. and Palmisano, G. and Sisti, M. and Pilati, T.},\ntitle={Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols},\njournal={Tetrahedron Asymmetry},\nyear={2003},\nvolume={14},\nnumber={11},\npages={1451-1454},\ndoi={10.1016/S0957-4166(03)00221-0},\nnote={cited By 29},\nurl={https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038060691&doi=10.1016%2fS0957-4166%2803%2900221-0&partnerID=40&md5=54c675f7ed410a92343e34f1502a144b},\naffiliation={Dipto. di Chim. Organ. e Industriale, Univ. degli Studi di Milano, Via Venezian 21, I-20133 Milano, Italy; Dipto. Sci. Chimiche Alimentari F., Univ. Piemonte Orientale 'A. A.', Via Bovio 6, I-28100 Novara, Italy; Dipto. Sci. Chimiche Fisiche M., Univ. degli Studi dell'Insubria, Via Valleggio 11, I-2210 Como, Italy; CNR-Ist. Sci. Tecnologie Molecolari, Via Golgi 19, I-20133 Milano, Italy},\nabstract={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. © 2003 Elsevier Science Ltd. All rights reserved.},\nkeywords={1,2 diamine [n,n' bis[1,7,7 trimethylbicyclo[2.2.1]hept 2 yl] 1,2 ethanediamine]; camphor; diamine; ester derivative; ligand; naphthol derivative; polycyclic aromatic hydrocarbon derivative; trifluoromethanesulfonic acid; unclassified drug, article; asymmetric synthesis; carbon nuclear magnetic resonance; crystal structure; drug synthesis; high performance liquid chromatography; oxidation; priority journal},\nchemicals_cas={camphor, 464-49-3, 76-22-2, 8008-51-3; trifluoromethanesulfonic acid, 1493-13-6},\nreferences={Lucet, D., Le Gall, T., Mioskowski, C., (1998) Angew. Chem., Int. Ed. Engl., 37, p. 2580; Whitesell, J.K., (1989) Chem. Rev., 89, p. 1581; Togni, A., Venanzi, L.M., (1994) Angew. Chem., Int. Ed. Engl., 33, p. 497; Tomioka, K., (1990) Synthesis, p. 541; Bennani, Y.L., Hanessian, S., (1997) Chem. Rev., 97, p. 3161; Nantz, M.H., Lee, D.A., Bender, D.M., Roohi, A.H., (1992) J. Org. Chem., 57, p. 6653; Kotsuki, H., Kuzume, H., Gohda, T., Fukuhara, M., Ochi, M., Oishi, T., Hirama, M., Shiro, M., (1995) Tetrahedron: Asymmetry, 6, p. 2227; Giovenzana, G.B., Pagliarin, R., Palmisano, G., Pilati, T., Sisti, M., (1999) Tetrahedron: Asymmetry, 10, p. 4277; Cabella, G., Jommi, G., Pagliarin, R., Sello, G., Sisti, M., (1995) Tetrahedron, 51, p. 1817; Raza, Z., Dakovic, S., Vinkovic, V., Šunjic, V., (1996) Croat. Chem. Acta, 69, p. 1545. , These authors reacted (1R)-camphor and ethylenediamine in toluene and in the presence of p-toluenesulfonic acid and obtained the diimine 2 in 61% yield; Jian, L.S., Aigiao, M., Guishu, Y., Yaozhong, J., (1992) Synth. Commun., 22, p. 1497; Periasamy, M., Devasagayaraj, A., Satyanarayana, N., Narayana, C., (1989) Synth. Commun., 19, p. 565; Ipaktschi, J., (1984) Chem. Ber., 117, p. 856; note; note; note; Rosini, C., Franzini, L., Raffaeli, A., Salvatori, P., (1992) Synthesis, p. 502; Nakajima, M., Miyoshi, I., Kanayama, K., Hashimoto, S., Noji, M., Koga, K., (1999) J. Org. Chem., 64, p. 2264. , and references cited therein; Smrčina, M., Poláková, J., Vyskočil, Š., Kočovský, P., (1993) J. Org. Chem., 58, p. 4534; Kozlowski, M.C., Li, X., Carrol, P.J., Xu, Z., (2002) Organometallics, 21, p. 4513; Li, X., Yang, J., Kozlowski, M.C., (2001) Org. Lett., 3, p. 1137; Hovorka, M., Ščigel, R., Gunterová, J., Tichý, M., Závada, J., (1992) Tetrahedron, 48, p. 9503; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G., Camalli, G., (1994) J. Appl. Crystallogr., 27, p. 435; Sheldrick, G.M., (1997) SHELX-97. Program for the Refinement of Crystal Structures, , University of Göttingen, Germany},\ncorrespondence_address1={Palmisano, G.; Dipto. Sci. Chimiche Fisiche M., Via Valleggio 11, I-2210 Como, Italy; email: giovanni.palmisano@uninsubria.it},\npublisher={Elsevier Ltd},\nissn={09574166},\ncoden={TASYE},\nlanguage={English},\nabbrev_source_title={Tetrahedron Asymmetry},\ndocument_type={Article},\nsource={Scopus},\n}\n\n","author_short":["Caselli, A.","Giovenzana, G.","Palmisano, G.","Sisti, M.","Pilati, T."],"key":"Caselli20031451","id":"Caselli20031451","bibbaseid":"caselli-giovenzana-palmisano-sisti-pilati-synthesisofc2symmetricaldiaminebasedon1rcamphorandapplicationtooxidativearylcouplingofnaphthols-2003","role":"author","urls":{"Paper":"https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038060691&doi=10.1016%2fS0957-4166%2803%2900221-0&partnerID=40&md5=54c675f7ed410a92343e34f1502a144b"},"keyword":["1","2 diamine [n","n' bis[1","7","7 trimethylbicyclo[2.2.1]hept 2 yl] 1","2 ethanediamine]; camphor; diamine; ester derivative; ligand; naphthol derivative; polycyclic aromatic hydrocarbon derivative; trifluoromethanesulfonic acid; unclassified drug","article; asymmetric synthesis; carbon nuclear magnetic resonance; crystal structure; drug synthesis; high performance liquid chromatography; oxidation; priority journal"],"metadata":{"authorlinks":{}}},"bibtype":"article","biburl":"https://cloud.alberti.top/index.php/s/xQ8igwraeGLfEPJ/download/scopus.bib","dataSources":["94TuW2BgcXBh3pgcY","3vf8ATvaZFv2FGt7R","irnS7ryEAzf9jZde2","LBbkvwYBGL2WNBwtp","7pF76B4jHaih5QEAT"],"keywords":["1","2 diamine [n","n' bis[1","7","7 trimethylbicyclo[2.2.1]hept 2 yl] 1","2 ethanediamine]; camphor; diamine; ester derivative; ligand; naphthol derivative; polycyclic aromatic hydrocarbon derivative; trifluoromethanesulfonic acid; unclassified drug","article; asymmetric synthesis; carbon nuclear magnetic resonance; crystal structure; drug synthesis; high performance liquid chromatography; oxidation; priority journal"],"search_terms":["synthesis","symmetrical","diamine","based","camphor","application","oxidative","aryl","coupling","naphthols","caselli","giovenzana","palmisano","sisti","pilati"],"title":"Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols","year":2003}