Two new efficient preparations of enantiopure 2,2′-dihydroxy-6,6′-dimethoxy-1,1′-biphenyl
✍ Scribed by Giovanna Delogu; Davide Fabbri
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 315 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
Two new useful methods for the preparation of diol 1 starting from available compounds are described. Separation of the two enantiomers entails resolution of racemic diol 1 via the corresponding diastereomeric N-methylated phosphorothioamidates. Their separation by recrystallization followed by reduction afforded diol (aS)-I and (aR)-I in 100% and 72% ee, respectively.
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The new chiral backbones (R)-(+)-and S-(-)-2-amino-2%-hydroxy-6,6%-dimethyl-1,1%-biphenyl and (R)-(+)-and (S)-(-)-2-amino-2%-hydroxy-4,4%,6,6%-tetramethyl-1,1%-biphenyl were synthesized from o-methylaniline and 2,4-dimethyl-aniline respectively in seven steps. A new resolution method was developed t
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