Journal
AUSTRALIAN JOURNAL OF CHEMISTRY
Volume 62, Issue 12, Pages 1661-1666Publisher
CSIRO PUBLISHING
DOI: 10.1071/CH09074
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Funding
- Slovenian Research Agency [P0-0502-0103, P1-0179, J1-6689-0103-04]
- Boehringer-Ingelheim Pharma GmbH Co. KG
- Krka d.d.
- Lek d.d.
- Sandoz company
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Regioselective copper(i) iodide-catalyzed cycloadditions of chiral pyrazolidin-3-on-1-azomethine imines 3a j to ethyl propiolate 4 gave cycloadducts 5a-h and 5'i and 5/5'j as single regioisomers. In terms of facial selectivity, cycloadducts 5a-h and 5'i were obtained as single diastereomers, whereas the reaction of dipole 3j was less selective and gave a mixture of 5j and 5'j in a ratio of 15:85. Stereoselectivity of copper(I) iodide-catalyzed cycloadditions of ethyl propiolate 4 to azomethine imines 3 was controlled by the stereodirecting phenyl group at position 5 and by the ortho-substituents at the 1'-Ar residue.
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