摘要
以L-苯丙氨基醇为原料合成一种新颖的3-苄基-5-正丁基环磺酰胺手性辅助试剂,将其酰化后应用于不对称羟醛缩合反应,具有很高的化学产率(85%～94%)和syn式非对映选择性(dr:92∶8～99∶1).羟醛缩合产物5a解脱后高产率得到近乎光学纯的产物(2S,3S)-3-羟基-2-甲基-3-苯基丙酸6a,同时可定量回收环磺酰胺手性辅助试剂.
A novel cyclosulfamiade chiral auxiliary was prepared starting from L phenylpropanotamine, which was used to induce asymmetric aldol reactions after acylation. The aldol reactions induced by chiral cyclosulfamiade occurred in good yields （85%- 94%） with high syn diastereoselectivities （dr： 92 ： 8-99 ： 1）. Aldol adduct 5a was readily cleaved by hydrolysis to afford almost enantiomerically pure （2S, 3S）-3-hydroxy-2-methyl-3-phenyl propionic acid 6a in good yield. The chiral auxiliary could be recovered quantitatively in this process.
出处
《湖北大学学报（自然科学版）》
CAS
2013年第1期98-103,共6页
Journal of Hubei University：Natural Science
基金
国家自然科学基金(21042005)资助
