Science of Synthesis

Markó, I. E.; Pospíšil, J., Science of Synthesis, (2010) 47, 105.

The term Julia alkenation defines an original two-step protocol employed for the formation of alkenes. In the first step, a β-hydroxy sulfone ‌6‌ (E = H) or its derivative ‌6‌ (E = Ac, Ms) is formed by reacting an anion generated α to a sulfone ‌5‌ (X = SO2Ph), sulfoxide ‌5‌ [X = S(O)Ph], or sulfoximide ‌5‌ [X = S(O)(NR5)Ph] and a carbonyl compound. This intermediate ‌6‌ is isolated and submitted to reductive elimination conditions (‌Scheme 2‌).

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M	(MM8)8Me	M	Me	MM8Me	Me	MeM8/MMMM	[‌88‌]
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M		M	MMe	MM8Me	Me	MeM8/MMMM	[‌88‌]
M	(MM8)8Me	M	(MM8)8Me	MMMe	Me	e-MeMe	[‌88‌]
M	eMe	Me	Me	MMMe	Me	MeM8/MMMM	[‌88‌]
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