Fluorinative hydrolysis of phosphorothioic acid esters with a binaphthyl group through axis-to-center chirality transfer leading to the formation of P-chiral phosphorothioic monofluoridic acid salts.
نویسندگان
چکیده
Asymmetric synthesis of P-chiral phosphorothioic monofluoridic acid ammonium salts was achieved via axis-to-center chirality transfer reactions by using phosphorothioic acid O-esters with a binaphthyl group, and the absolute stereochemistry of the salts was determined by X-ray analyses and by comparison of their CD spectra.
منابع مشابه
Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction
Enantiopure O-phenyl ethylphosphonothioic acid (1) was easily obtained by the enantioseparation of racemic 1, which was prepared from commercially available phosphorothioic trichloride through four steps. Enantiopure 1 was found to show an excellent chiral recognition ability for various 1-arylethylamine derivatives during the diastereomeric salt formation. Especially, enantiopure 1 could recog...
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Chiral monophosphines (MOPs), whose chirality is due to biaryl axial chirality, are prepared from enantiometrically pure 2,2%-dihydroxy-1,1%-binaphthyl and 3,3%-dihydroxy-4,4%-biphenanthryl. The representatives are 2-(diphenylphosphino)-2%-methoxy1,1%-binaphthyl (MeO–MOP and 3-(diphenylphosphino)-3%-methoxy-4,4%-biphenanthryl (MOP–phen). The palladium complexes coordinated with the MOP ligands ...
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Phosphorodiselenoic acid esters with a binaphthyl group were reacted with alkenes in the presence of Bu3SnH and AIBN to give phosphonoselenoic acid esters in moderate to good yields. The addition of a phosphoroselenoyl group to alkenes proceeded in an anti-Markovnikov fashion. The diastereoselectivity was improved by the introduction of substituents to 3,3'-positions of a binaphthyl group.
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ورودعنوان ژورنال:
- Chemical communications
دوره 50 83 شماره
صفحات -
تاریخ انتشار 2014