Dynamic Thermodynamic Resolution of Racemic 1,1'-Binaphthyl-2,2'-diol (BINOL).
Org Lett
; 26(10): 2129-2134, 2024 Mar 15.
Article
em En
| MEDLINE
| ID: mdl-38446080
ABSTRACT
A dynamic thermodynamic resolution method for converting (R/S)-BINOL (1,1'-binaphthyl-2,2'-diol) into (R)-BINOL in 100% theoretical yield is reported. This technique involves mixing (R/S)-BINOL with N-benzyl cinchonidinium bromide (1 equiv) and a [Cu2(tmeda)2(µ-OH)2]Br2 (2.5 mol %) redox catalyst in acetonitrile. In the background of this process is the observation that the energy for atropoisomerization decreases significantly when an electron is removed from BINOL. Therefore, it is possible to convert both enantiomers into the thermodynamically favorable [N-benzyl cinchonidinium bromide·(R)-BINOL] adduct.
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MEDLINE
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En
Ano de publicação:
2024
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Article