155498-78-5Relevant articles and documents
An organo-catalytic approach to the enantioselective synthesis of (R)-selegiline
Talluri, Siva Kumar,Sudalai, Arumugam
, p. 9758 - 9763 (2007)
An efficient enantioselective synthesis of (R)-selegiline has been achieved by two routes, via proline-catalyzed α-aminooxylation as well as α-amination of phenylpropanaldehyde as the key step.
Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis
RajanBabu,Nugent, William A.
, p. 986 - 997 (2007/10/02)
Bis(cyclopentadienyl)titanium(III) chloride reacts with epoxides by initial C-O homolysis. The regiochemistry of the opening is determined by the relative stabilities of the radicals. Depending on the reaction partners, these radicals undergo intramolecular (hex-5-enyl cyclization) or intermolecular additions to olefins. The resultant radicals are efficiently scavenged by a second equivalent of Ti(III) to afford the corresponding Ti(IV) derivative. Treatment of this intermediate with electrophiles such as H+ or halogens provides a route to functionalized cyclopentanes and other useful products. The radical initially formed from an epoxide can also be trapped by H-atom donors such as 1,4-cyclohexadiene or tert-butyl thiol, resulting in an overall reduction of the epoxide. In the absence of a H-atom donor or an olefin, this radical is trapped by Ti(III), resulting in a β-oxido-Ti organometallic species which undergoes facile elimination to give an olefin. The reaction conditions are remarkably mild and are applicable to very sensitive substrates.
