Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction

Shih I. Liu, Jia Yun Haung, Indrajeet J. Barve, Sheng Cih Huang, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

An enantioselective synthesis of iso-, isothio-, and isoselenohydantoin and diketopiperazine-fused tetrahydroisoquinolines from l-Dopa was reported. The route consists of an Pictet-Spengler reaction of (S)-2-amino-3-(3,4-dimethoxyphenyl)propanoates with various aldehydes to afford diastereomeric tetrahydroisoquinolines. Next step, the tetrahydroisoquinolines were further reacted with iso-, isothio-, or isoselenocyanates to construct hydantoin. Similarly, the diketopiperazine moiety was constructed by subjecting tetrahydroisoquinolines to a condensation reaction with chloroacetyl chloride followed by nucleophilic addition with various primary amines.

Original languageEnglish
Pages (from-to)336-344
Number of pages9
JournalACS Combinatorial Science
Volume21
Issue number4
DOIs
StatePublished - 8 Apr 2019

Keywords

  • Pictet-Spengler reaction
  • diketopiperazine - fused tetrahydroisoquinolines
  • enantioselective synthesis
  • hydantoin - fused tetrahydroisoquinolines
  • molecular hybridization

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