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′- …

Y Liang, S Gao, H Wan, J Wang, H Chen, Z Zheng…

Index: Liang, Yuxue; Gao, Shuang; Wan, Huihui; Wang, Junwei; Chen, Huilin; Zheng, Zhuo; Hu, Xinquan Tetrahedron Asymmetry, 2003 , vol. 14, # 10 p. 1267 - 1273

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Citation Number: 24

Abstract

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 ...