Catalytic Enantioselective Iodoaminocyclization of Hydrazones

Catalytic Enantioselective Iodoaminocyclization of Hydrazones

The first catalytic enantioselective iodoaminocyclization of β,γ-unsaturated hydrazones has been developed with the help of a trans-1,2-diaminocyclohexane-derived bifunctional thiourea catalyst and allows for the direct access to Δ2-pyrazolines containing a quaternary stereogenic center in high yiel...

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (12), p.3368-3371
Hauptverfasser: Tripathi, Chandra Bhushan, Mukherjee, Santanu
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclohexylamines - chemistry
Hydrazones - chemistry
Hydrocarbons, Iodinated - chemistry
Molecular Structure
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Stereoisomerism
Thiourea - chemistry
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Beschreibung
Zusammenfassung:The first catalytic enantioselective iodoaminocyclization of β,γ-unsaturated hydrazones has been developed with the help of a trans-1,2-diaminocyclohexane-derived bifunctional thiourea catalyst and allows for the direct access to Δ2-pyrazolines containing a quaternary stereogenic center in high yield with good enantioselectivity (up to 95% yield and 95:5 er).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5013982