Tetrahedron Letters

Nucleophilic addition of methyllithium to chiral oxime ethers: asymmetric preparation of 1-(aryl) ethylamines and application to a synthesis of calcimimetics (+)-NPS R- …

N Yamazaki, M Atobe, C Kibayashi

Index: Yamazaki, Naoki; Atobe, Masakazu; Kibayashi, Chihiro Tetrahedron Letters, 2001 , vol. 42, # 30 p. 5029 - 5032

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Citation Number: 45

Abstract

Chiral (E)-arylaldehyde oxime ethers, prepared using (R)-1-phenyl-1, 2-ethanediol as a chiral auxiliary, undergo nucleophilic addition with methyllithium to give diastereomerically enriched O-alkyl hydroxylamines which, after reductive N O bond cleavage, lead to the corresponding (R)-1-(aryl) ethylamines. This methodology has been applied to the enantioselective synthesis of a new type of arylalkylamine calcimimetics (R)-(+)-NPS R- ...

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