CHIRALITY TRANSFER IN THE ESTER ENOLATE CLAISEN REARRANGEMENT OF (R)-1-METHYL-(E)-2-BUTENYL HYDROXYACETATE AND ITS APPLICATION TO THE STEREOCONTROLLED PHEROMONE SYNTHESIS
- 5 October 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 13 (10) , 1669-1672
- https://doi.org/10.1246/cl.1984.1669
Abstract
The ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2-butenyl hydroxyacetate provides complete asymmetric transfer along with 98% erythroselectivity to give (2R,3S)-2-hydroxy-3-methyl-(E)-4-hexenoic acid. Its synthetic utility is demonstrated by the stereocontrolled synthesis of optically active pheromones.Keywords
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