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Syntheses and resolutions of new chiral biphenyl backbones: 2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′-biphenyl

✍ Scribed by Yuxue Liang; Shuang Gao; Huihui Wan; Junwei Wang; Huilin Chen; Zhuo Zheng; Xinquan Hu

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 241 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00217-9

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✦ Synopsis

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 to provide homochiral enantiomers (from diastereomeric salts) in reasonably high yields. The absolute configuration of the new biphenyls was confirmed by X-ray structural analysis.

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