The Julia olefination (also known as the Julia–Lythgoe olefination) is the chemical reaction of phenyl sulfones (1) with aldehydes (or ketones) to give alkenes (3) after alcohol functionalization and reductive elimination using sodium amalgam or SmI2. The reaction is named after the French chemist Marc Julia.
This transformation highly favors formation of the trans-alkene.
All four steps can be carried out in a single reaction vessel, and use of R3X is optional. However, purification of the sulfone intermediate 2 leads to higher yield and purity. Most often R3 is acetyl or benzoyl, with acetic anhydride or benzoyl chloride used in the preparation of 2.
Several reviews have been published.
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