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Stereoselective Synthesis of Bicyclic Nitrocyclopropanes by a Radical–Anion Domino Reaction
Author(s) -
Kamimura Akio,
Kadowaki Ayako,
Yoshida Takayuki,
Takeuchi Ryota,
Uno Hidemitsu
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901920
Subject(s) - domino , stereoselectivity , bicyclic molecule , intramolecular force , chemistry , sn2 reaction , radical cyclization , cyclopropanation , combinatorial chemistry , computer science , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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 S N 2 reaction.