317807-18-4Relevant articles and documents
Synthesis of enantiomerically pure helicene-like mono 1,3-oxazines from 1,1′-binaphthyl-2,2′,7-triol and study of their chiroptical properties
Sundar, M. Shyam,Bedekar, Ashutosh V.
, p. 46258 - 46269 (2016)
A method was developed to synthesize 1,1′-binaphthyl-2,2′,7-triol by an oxidative cross coupling reaction of 2-hydroxy naphthalene and 2,7-dihydroxy naphthalene. A process was optimized to separate the enantiomers of this compound by making its complex with S-brucine; its absolute configuration was established and it was converted into a series of helicene-like mono 1,3-oxazines. The chiroptical properties of these molecules were investigated and it was established that the helicene-like structural element contributes more to the optical rotation as compared to the stereogenic center.
Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes
Narute, Sachin,Parnes, Regev,Toste, F. Dean,Pappo, Doron
supporting information, p. 16553 - 16560 (2016/12/27)
Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.
