Science of Synthesis

Aggarwal, V.; Richardson, J., Science of Synthesis, (2004) 27, 70.

In 1958, Johnson and LaCount reported the first example of the reaction of a sulfur ylide with an aldehyde to give an epoxide.[‌12‌] In a seminal work four years later,[‌230‌] Corey and Chaykovsky reported the general application of sulfonium ylide ‌101‌ with a wide range carbonyl compounds to give epoxides ‌133‌ (‌Scheme 70‌); this addition–elimination reaction has become known as the Corey–Chaykovsky reaction and is clearly analogous to the epoxidation of carbonyl compounds using sulfoxonium ylides (see Section ‌27.1.2.2.1‌). The epoxidation of carbonyl compounds in this way is one of the most common applications of such species in organic synthesis. The epoxidation of such carbonyl species with sulfonium ylides represents a complimentary method to the Wittig alkenation followed by alkene oxidation that might otherwise be employed to achieve the same overall transformation.

‌Meeeee 88‌ Meeeeeeee ee eee Meeee–Meeeeeeee Meeeeeee[‌88‌]

M eeeeee ee eeeeeeeeee eeeeeeeeee eeeeeeeee eeeee eeeeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeeee,[‌8‌] eee e eeeeeee eeeeeeeeeee eeeeeeeeeeeee ee eee eeeeee ee eee eeeeee eee eeeeeeeeee eeeeeeeeee ee eee eeeee ee eee eeeeeeeeeee ee eeeeeeeee eee eeeeeee eee eeeeeeeee.[‌888‌] Mee eeeeeeeee eeeeeeee, (eeeee eee eeeeeeeee eeee eeeeee eeeeeeee) eee eeeee ee eeeeeeeee ee eeee eeee eee eeeeeeeeeeeee eeeeeee ee (8) eeeeeee eeeeeeeeee eeeeeeee ee eeeeeeeeeeeee ee (8) eeeeeeee ee eee eeeeeee eeee eeeeeeee eeeeeeeee ee eeeeeeeeee-eeeee-eeeeeeeee eeeeeeeeeeeee ee eeeee eeeeeeeee.

Meeeeeeeeeeeeeeee eeeeeeeee (‌888‌) ee e eeeeee eeeeeeee eeeeeeeee eeeeeeee eeeeeee eeee ee eeeeee eeeeeeee ee eeeeeee eeeeeeeee, eeee eeeeeeee eee eee eeeeeeeeeee ee eeeeeeee eeeeeeeee. Meeeeeeee, eeeeeeeee, eeeeeeeeeee, eee eeeeeeee eeeeeeeee eee eeeeeeeee, eeeeeeee, eee eeeeee eeeeeee, eee 8,8-eeeeeeeeee eeeeeeeee eee eee eeeeeee eeeeeeeee eeee eeeeeeee. Meeeeeeeeeeeeeeee eeeeeeeee (‌888‌) ee eeeeeeee eeee eeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeeeee (‌88‌) eee eeee ee eeee eeeeeeee eee eee eee eeeeeeee eeeee eeeee eeee eeeeeeeee eee eeeeeeeeeeeee eeeee-, eeeee-, eee eeeeeeeeeeeeeeeee.

Mee eeeeeee, eee ee eee eeeeeee eeeeeeeee, eeeeeeeeeeeeeeeeeee eeeeeeeee (‌88‌) eeeeee eeeeeeeeee eeee eee eeeeeeee eeeee ee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee eeee eeeeeee eee eeeeeeeeeeee (eee Meeeeee ‌88.8.8.8.8‌) eeeeee eeeeeeeeeeeeeeeee eeeeeeeee (‌888‌) eeeeeeeee eeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeee ee α,β-Meeeeeeeeee Meeeeeee Meeeeeeee eeee Meeeee Meeeee

Mee ee eee eeeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee eeee, ‌88‌ eee ‌888‌ eeeee eeee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeeee. Mee eeeeeee, eeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeee (‌88‌) eeee 8-eeee-eeeeeeeeeeeeeeeeee eeeee eeeeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeee eee-eeeeeee eee-‌88‌, eeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee (‌888‌) eeeee eee eeeee-eeeeee eeeee-‌88‌ eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee-Meeeeeeeee Meeeeeeeeeeeeeeeee Meeeeeeeeee[‌88‌]

Mee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eeeeee eeee eeeeeeeee eee eeeeeee eeeeeeee e eeeeeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeee. M eeeeeee ee eeeee eeeeeeeeeeee eee eeeeeeeee, eee eee eeeeee ee eee eeeeeeeeeee eeeeee eeeeeee ee eee eeeee ee eeeeeeee ee eee eeeeeee ee eee eeeeeeee. Mee eeeeeee, eeeeeeeee eeeeee eeeeeeeeee ee ee eeeee eeeee eeeee eeee eeeeeeeee ee eeee eeeeeeee eeee eeeeeeee eeeee eeeeeeeeeee, eeeeeee eeeee eeee eee eeeeeeeeee ee eeee eeeeeeee eeeeeeee-eeeeeeeeeee eeeeee, eeee ee ee eeeee ee eeeeee eeeee, eee eeeeeeeee eeeeeeeeee eeeeeee eeee eeeeeeee eeeeeeeee. Meee eeee eeeee eeee eeeeee eeeeeeeee eeeeeeee eeeeeeee eeee ee 8,8-eeeeeeeeee eeeeeeeee.[‌888‌]

Meeee-eeeeeeeeee eeeeee ee eeeee eeee eeeeeeeee eeee eeeee eeeeee eeeeeeeee ee eeee ee e eeee.[‌888‌,‌888‌] Mee eeeee eeeeeeee eeee ee eee eeee ee eeeeeeee ee eee eeeeeee, ee eee eeeeeeee ee eeeeeeee ee eeeee ee eee eeeee eeeeeee eee eeeeeeee eee eeeeeee eeeeeeeeeeee eeeeeeee eeeeeee eee eeee.

Meeeeeee-eeeeeeeeeee eeeeeeeee eeeeee eeeeeee eeeeee eeeeeeee eeee e eeeeeee ee eeeeeeeee eee eeeeeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeee eeeeeeee. Meeeeeee eeee eeeeeeeee ee eeeeeee eeeee eeeeeeeeee eeeee eeeeeeee eeee eeee eeeee eeeeeeeeeeeeeeeeeeee. Meee ee e eeeeee ee eee eeeeeeeeee eeeeeeeee ee eee-eeeeeee ‌888‌ eee eeeeeeeeeeee eeeeeeeee ee eeee-eeeeeee ‌888‌. Mee eeeeeeee eeeeeeeeeeeeeee ee eeeee eee eeeeeeee eee eeee eeeee ee ee e eeeeeeeeeee ee eee eeeeeeeee eeeeeeee eeeeeee eeee eeeeeeee eee eeeeeeeee eeeeee eeeeee eeeeeee ‌888‌ eeee eeeeeeee eeeeeee ‌888‌ eeeee eeeeee eeee eee eeeeeeeeee ee eeeeeeeee ‌888‌ eeee ‌888‌ (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeee ee Meeeeeeeeeeeeeee ee Meeeeeee ee Meeeeeeeeeee eeee Meeeee-Meeeeeeeee Meeeeeeee Meeeee[‌888‌]

Meeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeee eee eeeeeeeeee eeeeeeeeee ee eeee eee eeeeeeee eee eeeee eeeeeeee eeeeeeee eee eeeeeee eeeeeeeee eee ee eeeeeeeeeee eee eeeeee eeee eeee eeee ee eee eeeeee ee eee eeeeeeeee eeeeeeee eeeeeeeeee eeeeee eee ee eee eeeeee eeeee eeeeeeee ee eee eeeeeeee eeeeeeeee eeeeeeeeeeee.[‌888‌] Meee eeeeeeeeee eeeeee, eeee ee eeeee eeee eeeee eeeeeeeeeee eeeeee, eeeeeee eeeeeeeeee eeeeeeeeee eeeeeeee ee eeeeeeeee eee eeee eeee eeeeeeeeeee eeeee-eeeeeeee eee eee eeeee ee eeeeeeee eeeeeeee eeeeeeee. Mee eeeee ee eeeeeeeee eeee eee ee eeeeeeeee eeee eeeeeeee ee eeee eeeeee ee eeeeeeeeeeee.

Mee eeeeeeee ee ee α-eeeee eeeee eeeeeee eee eeeeee ee eee eeeeeeee. Mee eeeeeee, eeeeeeeeeeeeeeeee (eeeeeeeeeeeeee)eeeeeeeee (‌888‌) eeeeee eeee eeeeeeeeeeeee ee eeee ee eeeeeeeeeeee eeeeeee ‌888‌ eeee eeee eee eeeeeeeee eeeeeeee eeeeeee eee eeeeeee eeeeeeeee e Meeeeeee-eeee eeeeeeeeee eeeeeeee, eeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeeeee eeee ee eeee [(eeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeee (‌888‌) (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeee-Meee Meeeeeeeee ee ee Meeeeeeeeeee Meeeeee[‌888‌]

Me eee eeeeeeee ee eeeeee eeeeeeeeeeeeeeeee eeeeeeeee (‌888‌), eee eeeeeeeeeeeee eeeeeee eee eeeeeee eeee eeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeee ee eeeeeee eeeeeee.[‌888‌,‌888‌] Meeeeeeeeeeeeeeeeee eeeeeeeee (‌88‌) eeee eee eeeeeee eee eeee eeeeeeeeeeeeee eee ee eeeeeee ee eeeeee eeeeeee (eee Meeeeee ‌88.8.8.8.8‌). Me eeeee eee eeeee eeeeeeee ee eee eeeeeeeeeee eeeee eeeeeee ee eeee eeeeeeeeeee eee eeee eeeeee eeee eeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 888.