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An Effective and Useful Synthesis of Enantiomerically Enriched Arylglycinols
Author(s) -
Bandini Marco,
Cozzi Pier Giorgio,
Gazzano Massimo,
UmaniRonchi Achille
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1937::aid-ejoc1937>3.0.co;2-2
Subject(s) - chemistry , enantiomer , vicinal , amide , absolute configuration , organic chemistry , resolution (logic) , combinatorial chemistry , chromatographic separation , molecule , high performance liquid chromatography , artificial intelligence , computer science
A two‐step synthesis of racemic arylglycinols, together with a simple and straightforward methodology for their resolution, is described. This method constitutes a practical means of preparing racemic and optically pure electron‐rich or electron‐poor substituted arylglycinols, useful building blocks for the synthesis of biologically active molecules and chiral ligands. All of the chiral β‐amino alcohols 5 − 8 were isolated in good chemical yields and with excellent enantiomeric excesses: up to 99% in the cases of the arylglycinols 7 and 8 . Chiral fluoroaromatic vicinal amino alcohols can also be obtained with good enantiopurity using such a procedure. The key step of the strategy presented is an easy chromatographic separation of the diastereoisomeric amides prepared from acetyl mandeloyl chloride. The absolute configuration of the perfluorinated amino alcohols 5 was determined by X‐ray analysis of the corresponding amide 14a .