Synthesis of Enantiopure 1??Aryl??1??butylamines and 1??Aryl??3??butenylamines by Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (R)?? …

…, M van der Sluis, JW Nieuwenhuijzen…

Index: Dalmolen, Jan; Van Der Sluis, Marcel; Nieuwenhuijzen, Jose W.; Meetsma, Auke; De Lange, Ben; Kaptein, Bernard; Kellogg, Richard M.; Broxterman, Quirinus B. European Journal of Organic Chemistry, 2004 , # 7 p. 1544 - 1557

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Citation Number: 11

Abstract

Abstract The synthesis of enantiopure 1-aryl-1-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves:(a) formation of the chiral imines;(b) asymmetric addition of the allylzinc reagent;(c) removal of the chiral auxiliary by means of a reductive or non-reductive method. The reductive method provides 1-aryl-1- ...