TY - JOUR
T1 - Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction
AU - Liu, Shih I.
AU - Haung, Jia Yun
AU - Barve, Indrajeet J.
AU - Huang, Sheng Cih
AU - Sun, Chung-Ming
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/4/8
Y1 - 2019/4/8
N2 - 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.
AB - 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.
KW - Pictet-Spengler reaction
KW - diketopiperazine - fused tetrahydroisoquinolines
KW - enantioselective synthesis
KW - hydantoin - fused tetrahydroisoquinolines
KW - molecular hybridization
UR - http://www.scopus.com/inward/record.url?scp=85062842637&partnerID=8YFLogxK
U2 - 10.1021/acscombsci.9b00005
DO - 10.1021/acscombsci.9b00005
M3 - Article
C2 - 30839194
AN - SCOPUS:85062842637
SN - 2156-8952
VL - 21
SP - 336
EP - 344
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
IS - 4
ER -