Enantioselective oxidative biaryl coupling reactions catalyzed by 1, 5-diazadecalin metal complexes: efficient formation of chiral functionalized BINOL derivatives

X Li, JB Hewgley, CA Mulrooney, J Yang…

Index: Li, Xiaolin; Hewgley, J. Brian; Mulrooney, Carol A.; Yang, Jaemoon; Kozlowski, Marisa C. Journal of Organic Chemistry, 2003 , vol. 68, # 14 p. 5500 - 5511

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Citation Number: 220

Abstract

Chiral 1, 5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol% of a 1, 5-diaza-cis-decalin copper (II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3- substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. ...