【摘要】 以N-苄氧羰基-(S)-脯氨酸和5-(1-氨基烷基)四氮唑(烷基:甲基、乙基、2-苯基乙基)为原料,经两步反应合成了3个新颖的有机催化剂:(S)-5-脯氨酰胺基甲基四氮唑(3a),(S,S)-5-(1-脯氨酰胺基乙基)四氮唑(3b)和(S,S)-5-(1-脯氨酰胺基-2-苯基乙基)四氮唑(3c),并首次将其用于催化丙酮和含吸电子基芳香醛的不对称直接aldol反应.在室温条件下,催化剂3b表现出较好的催化活性,产物的ee值最高可达96%.更多还原

【Abstract】 Three novel organocatalysts (S)-5-prolylaminomethyltetrazole (3a), (S,S)-5-(1-prolylaminoethyl) tetrazole (3b) and (S,S)-5-(1-prolylamino-2-phenylethyl)tetrazole (3c) were readily prepared from N-benzyloxycarbonyl-(S)-proline and corresponding 5-(1-aminoalkyl)tetrazol (alkyl: methyl, ethyl and 2-phenylethyl) by the known reaction sequences in just two steps. Their catalytic performances were first evaluated in the asymmetric direct aldol reactions of acetone with electron-deficient aromatic aldehydes. At room temperature, the catalyst 3b displayed the efficient reactivity and the enantiomeric excess (ee) value of the products was up to 96%.更多还原