95671-30-0Relevant articles and documents
First asymmetric synthesis of (un)substituted bridged tetrahydro-2-benzazepines
Dumoulin, David,Lebrun, Stephane,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
, p. 195 - 201 (2010)
A new and flexible route for the asymmetric synthesis of a variety of alkylated bridged tetrahydro-2-benzazepines has been developed. The key steps are the highly diastereoselective Michael addition of metalated SAMP-hydrazones to α,β-unsaturated esters combined with cyclomethylenation/Mitsunobu coupling reactions to secure the formation of the seven-membered azaheterocycle and of the bridged unit, respectively.
ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-/RAMP-HYDRAZONES ANTI-DIASTEREO- AND ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED 5-OXO-ALKANOATES
Enders, Dieter,Papadopoulos, Kyriakos,Rendenbach, Beatrice E.M.,Appel, Rolf,Knoch, Falk
, p. 3491 - 3494 (2007/10/02)
An efficient and highly anti-diastereo-(de=90-100percent) and enantioselective (ee=92-100percent) synthesis of 3,4-disubstituted 5-oxo-alkanoates 3 in good overall chemical yields is described.The procedure involves the asymmetric Michael addition of aldehydes or ketones to enoates via their lithiated SAMP-/RAMP-hydrazones.Both enantiomers are accessible at will.