Efficient Routes to Racemic and Enantiomerically Pure (S)-BINOL Diesters

Abstract

A systematic study for esterification procedures to the synthesis of BINOL diesters is described. Reaction conditions with TFAA and 85% H 3 PO 4 were selected as the best procedure to prepare enantiomerically pure (S)-BINOL diesters VIII to XI with almost quantitative yields and very low reaction times.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s):Full experimental and spectral details.]

Synthesis, Characterization and Antifungal Assessment of Optically Active Bis-organotin Compounds Derived from (S)-BINOL Diesters

“…The solvents used were distilled and dried in accordance with standard procedures. Di-n-butyl-and diphenyltin dihydride were obtained by the reduction of the corresponding dichloride with lithium aluminum hydride [28] and the starting BINOL unsaturated diesters were prepared as described previously [15]. Thin layer chromatography was performed on Merck silica gel 60 F254 plates and visualization was accomplished with UV light and/or 5% ethanol solution of phosphomolybdic acid.…”

“…Taking into account that bis-chlorostannanes Ph 2 ClSn-R-SnClPh 2 show interesting biological activities [14], we present here the synthesis and antifungal assessment of optically active organotin compounds derived from (S)-BINOL as part of our research work on the behavior of C2 symmetry diol diesters in radical hydrostannations [15]. The aim of these studies was to determine the scope and limitations of the change in the structural core of the chiral diol over the stereoselectivity in the radical tandem cyclohydrostannation, which lead to eleven-membered macrodiolides [16 -18].…”

Mono- and diorganotin derivatives of (S)-BINOL diesters as precursors of C₂ symmetry chiral catalysts

“…Taking all this information into account, we decided then to study the hydrostannation reaction to four (S)-BINOL unsaturated diesters 8 (1,1'-binaphthyl-2-2´-diyl diacrylate; 1,1´-binaphthyl-2-2´-diyl dimethacrylate; 1,1´-binaphthyl-2-2´-diyl-(Z)-2-methyl-3-phenyl-2-propenoate and 1,1´-binaphthyl-2-2´-diyl di-(Z)-2,3-diphenyl-2-propenoate).…”