Synthesis of optically pure (R)- and (S)-tetrahydroisoquinoline-1- and -3-carboxylic acids was written by Kurata, Kaoruko;Inoue, Kumiko;Nishimura, Kazuhiko;Hoshiya, Naoyuki;Kawai, Nobuyuki;Uenishi, Junichi. And the article was included in Synthesis in 2015.Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid This article mentions the following:
The synthesis of (R)- and (S)-tetrahydroisoquinoline-1-carboxylic acids was achieved from N-Boc-protected (R)- and (S)-1-propenyltetrahydroisoquinoline (Boc = tert-butoxycarbonyl), resp., 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. In the experiment, the researchers used many compounds, for example, (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid).
(S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (cas: 151004-92-1) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Recommanded Product: (S)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem