Author/Authors :
Jiménez، نويسنده , , Jacqueline and Meza-Leَn، نويسنده , , Rosa L. and Sartillo-Piscil، نويسنده , , Fernando and Meléndez، نويسنده , , Francisco J. and Sansinenea، نويسنده , , Estibaliz and Ortiz، نويسنده , , Aurelio، نويسنده ,
Abstract :
A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the γ-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds.
