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Indolyl substituted 4-oxobut-2-enoic acids. Synthesis and aza-Michael additions

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Berkeš D., Koren̆ová A., Šafár̆ P., Horváthová H., Prónayová N.
Open Chemistry
|
2007
|
vol. 5
|
issue 3
688-705
EN
The synthesis of three new substituted 4-hetereoaryl-4-oxobut-2-enoic acids with indole ring substitutedin positions 3-, 5- and 7- is described. The addition of these Michael acceptors to 4-(1-phenylsulphonylpyrrol-3-yl)-4-oxobut-2-enoic acid in conjugate addition was explored using both racemic and chiral amines. In tandem with the crystallization-induced asymmetric transformation (CIAT) protocol the effective methodology for the synthesis of enantiomerically highly enriched substituted 2-amino-4-heteroaryl-4-oxobutanoic acids as multifunctional homotryptophan analogues was developed. [...]
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