Synthesis of Optically Pure (R)- and (S)-Tetrahydroisoquinoline-1- and -3-Carboxylic Acids
Synthesis of Optically Pure (R)- and (S)-Tetrahydroisoquinoline-1- and -3-Carboxylic Acids
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DOI：
10.1055/s-0034-1380289
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发表时间：
2015-03
期刊：
影响因子：
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通讯作者：
Kaoruko Kurata;Kumiko Inoue;K. Nishimura;N. Hoshiya;N. Kawai;J. Uenishi
中科院分区：
文献类型：
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作者：
Kaoruko Kurata;Kumiko Inoue;K. Nishimura;N. Hoshiya;N. Kawai;J. Uenishi
摘要以N-Boc保护的(R)-和(S)-1-丙烯基四氢异喹啉为原料，经过臭氧分解、NaBH4还原、氧化和N-Boc基团脱保护三步反应，分别合成了(R)-和(S)-四氢异喹啉-1-羧酸。同样，从n - boc保护的(S)-3-（4-苯基丁烯基）四氢异喹啉中得到(S)-四氢异喹啉-3-羧酸。该合成路线实用高效地提供了对映体纯的四氢异喹啉环基环氨基酸。
Abstract The synthesis of (R)- and (S)-tetrahydroisoquinoline-1-carboxylic acids was achieved from N-Boc-protected (R)- and (S)-1-propenyltetrahydroisoquinoline, respectively, in a three-step sequence of ozonolysis, NaBH4 reduction, oxidation, and deprotection of the N-Boc group. Similarly, (S)-tetrahydroisoquinoline-3-carboxylic acids were obtained from N-Boc-protected (S)-3-(4-phenylbutenyl)tetrahydroisoquinolines. This synthetic route provides tetrahydroisoquinoline ring-based cyclic amino acids in enantiomerically pure form in a practical and efficient manner.