Enders D, Kirchhoff J H, Köbberling J, Peiffer T H
Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule Aachen, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany.
Org Lett. 2001 Apr 19;3(8):1241-4. doi: 10.1021/ol015721x.
[reaction: see text]. Two novel chiral hydrazine resins for asymmetric solid-phase synthesis have been developed. The enantiopure beta-methoxyamino auxiliaries, derived from trans-4-hydroxy-(S)-proline and (R)-leucine, were attached to Merrifield resin and transformed into their corresponding hydrazines. Immobilization of various aldehydes, followed by 1,2-addition of organolithium reagents to the resulting enantiopure hydrazones and reductive cleavage from the solid support, furnished alpha-branched amines, which were isolated as their corresponding amides in good overall yields and enantiomeric excesses of up to 86%.
[反应：见正文]。已开发出两种用于不对称固相合成的新型手性肼树脂。源自反式-4-羟基-(S)-脯氨酸和(R)-亮氨酸的对映体纯β-甲氧基氨基助剂与Merrifield树脂相连，并转化为相应的肼。固定各种醛，然后将有机锂试剂对所得对映体纯腙进行1,2-加成并从固相载体上进行还原裂解，得到α-支链胺，其以相应的酰胺形式分离出来，总收率良好，对映体过量高达86%。
