Pavé Grégoire, Usse-Versluys Stéphanie, Viaud-Massuard Marie-Claude, Guillaumet Gérald
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, BP 6759, 45067 Orléans Cedex 2, France.
Org Lett. 2003 Nov 13;5(23):4253-6. doi: 10.1021/ol0353215.
[reaction: see text] Enantiomerically pure 5-acetyl-3-amino-3,4-dihydro-2H-1-benzopyran and methyl 3-amino-3,4-dihydro-2H-1-benzopyran-5-carboxylate were successfully synthesized starting from d- or l-serine. The formation of the benzopyran ring involved a radical cyclization step. The enantiomeric purities of the final aminochroman derivatives were determined by capillary electrophoresis using beta-cyclodextrins as a chiral selector.
[反应：见正文] 从d-或l-丝氨酸出发，成功合成了对映体纯的5-乙酰基-3-氨基-3,4-二氢-2H-1-苯并吡喃和3-氨基-3,4-二氢-2H-1-苯并吡喃-5-羧酸甲酯。苯并吡喃环的形成涉及一个自由基环化步骤。最终氨基色满衍生物的对映体纯度通过使用β-环糊精作为手性选择剂的毛细管电泳来测定。
