Enantioselective synthesis of primary 1-(aryl) alkylamines by nucleophilic 1, 2-addition of organolithium reagents to hydroxyoxime ethers and application to …

M Atobe, N Yamazaki, C Kibayashi

Index: Atobe, Masakazu; Yamazaki, Naoki; Kibayashi, Chihiro Journal of Organic Chemistry, 2004 , vol. 69, # 17 p. 5595 - 5607

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Citation Number: 68

Abstract

(E)-Arylaldehyde oxime ethers bearing a (1 S)-2-hydroxy-1-phenylethyl or (2 R)-1-hydroxy-2- phenylethyl group as a chiral auxiliary, both derived from a single precursor, methyl (R)- mandelate, underwent nucleophilic addition with organolithium reagents via six-membered chelates to give the diastereomerically enriched (R)-and (S)-adducts, respectively, which, after chiral auxiliary removal by reductive NO bond cleavage, led to the corresponding (R) ...

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