ChemInform Abstract: Asymmetric α-Alkylation of α,β-Unsaturated Esters. Application to the Synthesis of (R)-Lavandulol, (R)-Sesquilavandulol and Related Trifluoromethyl Compounds.

✍ Scribed by S. Faure; O. Piva

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199914213

✦ Synopsis

Asymmetric α-Alkylation of α,β-Unsaturated Esters. Application to the Synthesis of (R)-Lavandulol, (R)-Sesquilavandulol and Related Trifluoromethyl Compounds.

-Moderate diastereoselectivities are achieved in the alkylation of α,β-unsaturated esters (I) employing diacetone D-glucose as removable chiral auxiliary. The resulting esters (III) are easily reduced to (R)-lavandulol (IVb) and (R)-sesquilavandulol (IVa). When the same reaction is performed with trifluoromethyl derivatives (V), no significant diastereoselectivity is observed, probably due to an increase of the proton acidity in α-position of the carboxylic group in products (VI). -(FAURE, S.;