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2004
Amines
Q 0120
51- 068
Enantioselective Synthesis of Primary 1-(Aryl)alkylamines by Nucleophilic
1,2-Addition of Organolithium Reagents to Hydroxyoxime Ethers and Application to Asymmetric Synthesis of G-Protein-Coupled Receptor Ligands. —
Oximes (I) and (VIII), both derived from methyl (R)-mandelate, are converted into diastereomerically enriched adducts by addition of organolithium compounds. After removal of the chiral auxiliary by N—O bond cleavage the latter give the desired (R)and (S)-amines. Both enantiomers of hydroxyphenyl(ethyl)amine (V), previously used
as an efficient chiral auxiliary, are obtained by this method. The synthetic utility of the
present method is further demonstrated by the synthesis of calcium receptor agonist
NPS R-568 (VIc) and its thio analogue (VIh), and by transformation of vinyl derivative
(R)—(IVg) into NK-1 receptor antagonists CP-99,994 and CP-122,721 (VII). —
(ATOBE, M.; YAMAZAKI, N.; KIBAYASHI*, C.; J. Org. Chem. 69 (2004) 17,
5595-5607; Sch. Pharm., Univ. Pharm. Life Sci., Hachioji, Tokyo 192, Japan; Eng.)
— Klein
2004
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