107866-11-5Relevant articles and documents
Oxidative coupling of 2-substituted 1,2-dihydro-1-naphthols using Jones reagent: A simple entry into 3,3′-disubstituted 1,1′-binaphthyl-4, 4′-diols
Fillion, Eric,Trépanier, Vincent E.,Mercier, Lauren G.,Remorova, Anna A.,Carson, Rebekah J.
, p. 1091 - 1094 (2005)
2-Substituted 1,2-dihydro-1-naphthols underwent regioselective oxidative dimerization, when treated with Jones reagent, to furnish 3,3′- disubstituted 1,1′-binaphthyl-4,4′-diols. A series of symmetrical binaphthols were prepared and it was shown that the coupling reaction proceeds via the sequential oxidation of 2-substituted 1,2-dihydro-1-naphthols to 2-substituted 1-naphthols, which oxidatively dehydrodimerized.
Asymmetric hydroxylative phenol dearomatization promoted by chiral binaphthylic and biphenylic iodanes
Bosset, Cyril,Coffinier, Romain,Peixoto, Philippe A.,El Assal, Mourad,Pouysegu, Laurent,Quideau, Stephane,Miqueu, Karinne,Sotiropoulos, Jean-Marc
supporting information, p. 9860 - 9864,5 (2014/10/15)
The long-standing quest for chiral hypervalent organoiodine compounds (i.e., iodanes) as metal-free reagents for asymmetric synthesis continues. Although remarkable progress has recently been made in organoiodine-catalyzed reactions using a terminal oxidant in stoichiometric amounts, there is still a significant need for "flaskable" chiral iodane reagents. Herein, we describe the synthesis of new iodobinaphthyls and iodobiphenyls, their successful and selective DMDO-mediated oxidation into either λ3- or λ5-iodanes, and the evaluation of their capacity to promote asymmetric hydroxylative phenol dearomatization (HPD) reactions. Most notably, a C2-symmetrical biphenylic λ5-iodane promoted the HPD-induced conversion of the monoterpene thymol into the corresponding ortho-quinol-based [4+2] cyclodimer (i.e., bis(thymol)) with enantiomeric excesses of up to 94 %.
