J. Peters, Michael Seppi, R. Fröhlich
2002
Citations
0
Influential Citations
32
Citations
Journal
Synthesis
Abstract
1-Aryl-1-alkenyl N,N-diisopropylcarbamates (1) are obtained from alkyl aryl ketones and N,N-diisopropylcarbamoyl chloride (CbCl) by heating with excess pyridine. These undergo facile syn-carbolithiation by alkyllithium/diamine and produce configurationally stable lithiated benzyl carbamates, which have been trapped with different electrophiles. If the reaction is carried out in the presence of chiral diamines, such as (-)-sparteine or (-)-α-isosparteine, moderate enantiofacial differentiation is observed.