Diastereoselective alkylations of oxazolidinone vinylogous glycolates
2012
Jiménez, Jacqueline | Meza-León, Rosa L. | Sartillo-Piscil, Fernando | Meléndez, Francisco J. | Sansinenea, Estibaliz | Ortiz, Aurelio
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.
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