Chemistry Letters

AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER—AN APPLICATION TO THE ASYMMETRIC SYNTHESIS …

M Asami, T Mukaiyama

Index: Asami, Masatoshi; Mukaiyama, Teruaki Chemistry Letters, 1983 , p. 93 - 96

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Citation Number: 28

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.

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