Synthesis of Optically Pure (R)- and (S)-Tetrahydroisoquinoline-1- and -3-Carboxylic Acids

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.

Key words

quinolines - amino acids - peptides - asymmetric synthesis - Lewis acids

• References

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