AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER - AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF exo-(+)-BREVICOMIN -

Article abstract of DOI:10.1246/cl.1983.93

α-benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo<3.3.0>octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.