Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans
The first method for the [3 + 2] annulation of donor acceptor aminocyclopropanes with aldehydes is reported. The reaction is catalyzed by iron trichlorlde on alumina in yields up to 99% and with excellent cis selectivities (up to >20:1) and represents a stereoselective and atom economic access to valuable 2-aminotetrahydrofurans, which constitute the core of DNA and RNA.
Keywords: Donor-Acceptor Cyclopropanes ; Aldol-Type Reaction ; Ring-Expansion Reaction ; Carbonyl-Compounds ; 2,2-Dialkoxycyclopropanecarboxylic Esters ; Diastereoselective Synthesis ; Organic-Synthesis ; Annulation
Record created on 2012-02-23, modified on 2016-08-09