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

• Authors: Dušan Berkeš , Anna Koren̆ová , Peter Šafár̆ , Helena Horváthová , Nadežda Prónayová
• Languages of publication: EN

Abstracts

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. [...]

Keywords

EN

Indole; indole-2-carboxylate; 4-oxobut-2-enoic acid; conjugate addition; crystallization-induced asymmetric transformation; homotryptophan

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2007
• Volume: 5
• Issue: 3
• Pages: 688-705

Dates

published

1 - 9 - 2007

online

26 - 4 - 2007

Contributors

author

Dušan Berkeš

• Department of Organic Chemistry, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

author

Anna Koren̆ová

• Department of Organic Chemistry, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

author

Peter Šafár̆

• Department of Organic Chemistry, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

author

Helena Horváthová

• Department of Organic Chemistry, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

author

Nadežda Prónayová

• Department of NMR spectroscopy and mass spectroscopy, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

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Identifiers

DOI

10.2478/s11532-007-0019-7