New Practical Synthesis of the Exceptional Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone

Abstract

Herein we describe a short and practical synthesis of the exceptional musk odorants (R)-muscone and (R,Z)-5-muscenone from a readily available achiral macrocyclic diketone. The key step of the synthesis is the first sodium N-methylephedrate mediated enantioselective aldol condensation reaction (up to 76% ee). This new type of reaction proceeds via a dynamic kinetic resolution of an aldol intermediate.

Keywords

• Aldol reaction
• Amino alcohol
• Asymmetric synthesis
• Dynamic kinetic resolution
• Elimination