Science of Synthesis

Markó, I. E.; Pospíšil, J., Science of Synthesis, (2010) 47, 142.

Interestingly, a highly efficient reductive elimination protocol for β-hydroxy sulfoximides has been known since 1979. At that time, it was found that the combination aluminum amalgam/acetic acid is applicable to a wide variety of β-hydroxy sulfoximides, e.g. ‌73‌ (‌Scheme 26‌).[‌14‌,‌116‌] These compounds were then converted into mono-, di-, and trisubstituted alkenes, e.g. ‌74‌, in good to excellent yields. Unfortunately, the reductive elimination generally furnishes the desired alkenes with generally poor E selectivity, compared to the alkenes from the corresponding sulfone derivatives.[‌3‌,‌14‌] Moreover, when diastereomerically pure β-hydroxy sulfoximides are used, mixtures of E- and Z-alkenes are still produced (‌Scheme 27‌). As a consequence, the sulfoximide-based Julia–Lythgoe alkenation protocol is seldom employed nowadays and used only for the synthesis of mono- or 1,1-disubstituted alkenes.

‌Meeeee 88‌ Meeeeeeee Meeeeeeeeee ee β-Meeeeee Meeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	Meeee (M/M)	Meeee (%)	Mee
M	Me	(MM8)88Me	–	88	[‌88‌]
M	Me		–	88	[‌88‌]
Me	Me	(MM8)8Me	88:88	88	[‌88‌]
Me			88:88	88	[‌88‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeeeee ee Meeeeeeeeeeeeeeeee Meee β-Meeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeee-8-eee [‌88‌, M8 = M; M8 = Me; M8 = (MM8)88Me]; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee(MM) eeeeeeee ee e eeeeee ee eeeeeeeee eee ee eeeee ee eeee eeeeeee. Meee eeeeee ee eeeeeeeeeeeee ee eeeee eeeee eeeee ee eeeeeee.

Me eee eeee ee eee β-eeeeeee eeeeeeeeeee ‌88‌ [M8 = M; M8 = Me; M8 = (MM8)88Me; 8.88 e, 88.8 eeee, 8.8 eeeee] ee MMM (88 eM) eee eeeee MeMM (88 eM) eee M8M (88 eM). Meeeeeee Me (8.8 e, 88 eeee, 8.88 e-eeee), eeeee eee eeee eeeeeee eee 8 eee eeee 8% ee MeMe8 (888 eM), eeeeeeee, eee eeeeee eeeeeeeeeeee eeee M8M eee MeMM, eee eeeee ee eee eeeeeee. Meeeeeee eee eeeeeeeee eeeee MMM eee eee eeee eee eeeeeeee eeeeeeee (8–8 e). Mee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee eee eeeeee eee eeeeee eeee MMM. Mee eeeeeeee eee eeeeeee eeee M8M (888 eM), eee eee eeeeeee eee eeeeeeeee eeee eeeeeee (8 × 888 eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee 88% ee MeMM (8 × 888 eM) eee M8M (888 eM), eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) ee eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 8.88 e (88%).

References