Rose Oxides: A Facile Chemo and Chemo‐Enzymatic Approach

Abstract

Nonracemic rose oxides were synthesized from racemic or nonracemic monoterpene alcohol citronellol by a novel chemo and chemo‐enzymatic route. After the key step of bromomethoxylation of citronellol, the intermediate was dehydrobrominated by a base, followed by an acid catalyzed demethoxylation along with cyclization to furnish rose oxides in high yield. The racemic dehydrobrominated precursor was also kinetically resolved using various lipases to produce nonracemic rose oxides.

Keywords:

• Bromomethoxylation
• cis‐ and trans‐rose oxides
• citronellol
• cyclization
• dehydrobromination
• lipases