AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER—AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF exo-(+)-BREVICOMIN—
- 5 January 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 12 (1), 93-96
- https://doi.org/10.1246/cl.1983.93
Abstract
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.Keywords
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