Kaoruko Kurata, Kumiko Inoue, K. Nishimura
Mar 12, 2015
Citations
1
Influential Citations
8
Citations
Journal
Synthesis
Abstract
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.