N-(甘氨酸薄荷酯)-(+)-樟脑亚胺在烷基化反应中的双手性诱导效应 |
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引用本文: | 刘桂兰,周昌友,朴虎日,吴兰均,宓爱巧,蒋耀忠. N-(甘氨酸薄荷酯)-(+)-樟脑亚胺在烷基化反应中的双手性诱导效应[J]. 化学学报, 1992, 50(1): 89-95 |
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作者姓名: | 刘桂兰 周昌友 朴虎日 吴兰均 宓爱巧 蒋耀忠 |
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作者单位: | 中国科学院成都有机化学研究所 |
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摘 要: | 本文报道了从(+)-樟脑与(+)或(-)-甘氨酸薄荷醇酯所得的亚胺的烷基化反应, 烷基化产物经水解得到(R)-氨基酸。与N-(特丁氧羰基亚甲基)-(+)-樟脑亚胺相比,由于存在匹配的双手性诱导效应, 而使N-[甘氨酸-(+)-薄荷酯]-(+)-樟脑亚胺烷基化的立体选择性有明显的提高(43.8-98%),而不匹配的N-[甘氨酸-(-)-薄荷醇酯]-(+)-樟脑亚胺烷基化的立体选择性明显降低。它们的甲基化都给出(S)-丙氨酸, 且立体选择性不受薄荷酯的构型影响。
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关 键 词: | 氨基酸 烷基化 立体选择性 甘氨酸 诱导效应 薄荷酯 樟脑亚胺 |
Double asymmetric induction in alkylation of the imines derived from(+)-camphor and (+)-or (-)-methyl glycinate |
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Abstract: | A double asym. induction effect has been observed in the alkylation of the imines derived from (+)-camphor and (+)- or (-)-menthyl glycinates. After hydrolysis of the alkylated intermediates, (R)-a-amino acids are obtained in 7.3-100% enantiomeric excess. Compared with the alkylation of the imine obtained from (+)-camphor of tert-Bu glycinate, the stereoselectivity of the alkylation of the (+)-menthyl imine is obviously enhanced. Using MeI as an alkylating reagent, (S)-alanine is obtained. |
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Keywords: | AMINO ACID ALKYLATION STEREOSELECTIVITY GLYCINE INDUCTIVE EFFECT |
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