Browsing by Author "Liu, Shih-I"

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Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction
(2019-04-01)
Liu, Shih-I
;
Haung, Jia-Yun
;
Barve, Indrajeet J.
;
Huang, Sheng-Cih
;
Sun, Chung-Ming
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.