[3+2] Redox-Neutral Cycloaddition of Nitrocyclopropanes with Styrenes by Visible-Light Photocatalysis

The first nitro‐group‐initiated redox‐neutral [3+2] cycloaddition of nitrocyclopropanes with alkenes by using visible‐light‐absorbing transition‐metal complexes was reported. High diastereoselectivities were observed for two quaternary carbon centers on the ring and validated by DFT calculations. Sp...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry : a European journal 2015-06, Vol.21 (27), p.9676-9680
Hauptverfasser: Wang, Chengfeng, Ren, Xiang, Xie, Hujun, Lu, Zhan
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The first nitro‐group‐initiated redox‐neutral [3+2] cycloaddition of nitrocyclopropanes with alkenes by using visible‐light‐absorbing transition‐metal complexes was reported. High diastereoselectivities were observed for two quaternary carbon centers on the ring and validated by DFT calculations. Spiro‐ or polycyclic structures can be constructed smoothly. Cyclic γ‐amino acid derivatives and polysubstituted cyclic amino alcohols can be obtained easily through reduction of the nitro group. Constructing rings: The first nitro‐group‐initiated redox‐neutral [3+2] cycloaddition of nitrocyclopropanes with alkenes by using visible‐light‐absorbing transition‐metal complexes is reported. High diastereoselectivities were observed for two quaternary carbon centers on the ring. Spiro‐ or polycyclic structures can be constructed smoothly. Cyclic γ‐amino acid derivatives, which are potential precursors to peptidic oligomers and polysubstituted cyclic amino alcohols, can be obtained easily through reduction of the nitro group.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201500873