245674-29-7Relevant academic research and scientific papers
Diastereofacial selectivity in ketene [2+2] cycloaddition to endocyclic enecarbamates bearing a chiral auxiliary. Synthesis of the (-)-Geissman-Waiss lactone
Miranda, Paulo Cesar M. L.,Correia, Carlos Roque D.
, p. 7735 - 7738 (1999)
The diastereofacial selectivity of enecarbamates bearing a chiral auxiliary was evaluated for the [2+2]cycloaddition with dichloroketenes. Diastereofacial selectivity ranged from zero (bornyl and menthyl) to 60% (Greene's auxiliary and 8-phenylmenthyl). Chromatography separation of the diastereomeric azacyclobutanones derived from the 8-phenylmenthyl enecarbamate permitted an enantiodivergent synthesis of the (-)-Geissman-Waiss lactone, a key intermediate in the synthesis of necine bases.
