Journal
TETRAHEDRON LETTERS
Volume 72, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153063
Keywords
1,2,3,4-Tetrahydroquinolines; Aza-Diels-Alder reaction; Benzoylacetonitrile; Knoevenagel; One-pot domino
Categories
Funding
- Ministry of Science and Technology, Taiwan [MOST 108-2113-M-277-001]
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A diastereoselective aza-Diels-Alder reaction has been developed between in situ generated 2-aminophenyl-substituted enones and alpha-cyano-alpha,beta-unsaturated aromatic ketone. Highly substituted tetrahydroquinolines with an all-carbon quaternary center were prepared as both exo and endo isomers with excellent diastereoselectivity and high yields under very mild conditions.
Diastereoselective aza-Diels-Alder reaction between in situ generated 2-aminophenyl-substituted enones and alpha-cyano-alpha,beta-unsaturated aromatic ketone has been developed. In the presence of TEA as a catalyst prepared highly substituted tetrahydroquinolines with an all-carbon quaternary center in an in situ fashion. Both tetrahydroquinoline isomers (exo and endo) with excellent diastereoselectivity and high yields were synthesized in very mild conditions. (C) 2021 Published by Elsevier Ltd.
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