Stereoselective Synthesis of Bicyclic Nitrocyclopropanes by a Radical–Anion Domino Reaction

A novel one‐step radical‐ionic cyclopropanation was carried out to prepare aza‐ or oxabicyclo[3.1.0]hexane from β‐nitroamides or β‐nitroethers in a stereoselective manner (see scheme). The present procedure involves a higher‐order domino process that includes one‐electron oxidation– radical cyclizat...

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Veröffentlicht in:	Chemistry : a European journal 2009-10, Vol.15 (40), p.10330-10334
Hauptverfasser:	Kamimura, Akio, Kadowaki, Ayako, Yoshida, Takayuki, Takeuchi, Ryota, Uno, Hidemitsu
Format:	Artikel
Sprache:	eng
Schlagworte:	Anions Catalysis Combinatorial Chemistry Techniques Cyclization cyclopropanes Cyclopropanes - chemical synthesis Cyclopropanes - chemistry domino reactions Molecular Structure Nitro Compounds - chemical synthesis Nitro Compounds - chemistry oxidation Oxidation-Reduction radical cyclization Stereoisomerism stereoselective reaction
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Beschreibung
Zusammenfassung:	A novel one‐step radical‐ionic cyclopropanation was carried out to prepare aza‐ or oxabicyclo[3.1.0]hexane from β‐nitroamides or β‐nitroethers in a stereoselective manner (see scheme). The present procedure involves a higher‐order domino process that includes one‐electron oxidation– radical cyclization–intramolecular SN2 reaction.
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.200901920