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.