Science of Synthesis

Friesen, R. W.; Sturino, C. F., Science of Synthesis, (2006) 8, 841.

General Introduction

α-Lithio vinyl ethers ‌1‌ are useful reagents for organic synthesis, predominantly as nucleophilic reagents that react with a wide range of electrophiles and thus serve as acyl anion synthons ‌2‌ (‌Scheme 1‌). A number of reviews[‌1‌,‌2‌] on the preparation and chemistry of this class of vinyllithium reagent have appeared following the recognition of the synthetic utility of these reagents in the early 1970s by Schollkopf[‌3‌] and Baldwin.[‌4‌] Details regarding their use as acyl anion synthons, and in other synthetic transformations, can be found in Sections ‌8.1.27.4‌–‌8.1.27.10‌.

‌Meeeee 8‌ α-Meeeee Meeee Meeee Meeeeeee

Meeeeeee α-eeeeee eeeee eeeee eeeeeeee eee eeeeeeeee eeeeeeee ee eee eeeeeeeeeee eee eeee ee eeee eeeeeee eeeeeeeee ee eeeeeeeeeeee, eeeeeeeeee 8-eeeeeeeeeeeeeeeeeee (‌8‌, M8 = Me), ee eeee ee 8-eeeeee-8,8-eeeeeeeeeeee eee 8-eeeeee-8,8-eeeeeee-8M-eeeee, eeee eeee eeeeeeee eee eeeeeeee ee eeeeee.[‌8‌–‌8‌] M eeeeee ee α-eeeeee eeeee eeeee eeeeeeee eeee eeee eeeeeeeeeeeee ee 88M MMM eeeeeeeeeeee.[‌8‌,‌8‌] Mee eeee eeeeeeeeeeeeee eeeeeee ee eeee ee eeeee eeeeeee ee eee eeeee eeeeeeeee eeeee (δ 88–88) ee eee eeeeeeeee eeeeee eeee eeeeeeeee (δ 888–888) eeeeeeee ee eee eeeeeeeeeeeee eeeeee eeeeeeeee ee eee eeeeeeee ee eee eeeeee eeeee eeeee (δ 888–888). M eeeeeeeee eeeee eeee ee eeeeeee ee eeeeeeeee (8–88 eee) ee eeee eeeeeeee eee eee β-eeeee eeeeee eeee eeeeeeeee, eeeee eee eeeeeeeee ee eee eeeeeeeee eeeeee eeeeeeee ee eeeeee ee eeeeeeee eeeeeee eeeeeee (8–8 eee). Meeeeeeee, ee eee 88M MMM eeeeeeee ee (8-eeeeeeeeeeee-8,8-eeeeee)eeeeeee, eee eeeeeeeee M8 eeeeeeeee (δ 888) ee eeeeeee ee. 88 eee eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee (δ 888).[‌8‌] Meeee e eeeeeeeeeee ee 88M, 8Me, 8M MMMMM MMM, eee MM eeeeeee, (8-eeeeeeeeeeee-8,8-eeeeee)eeeeeee ee eeeeeeeeeeeeeee eee eeeee ee eeeee ee e eeeee eeee e eeeeeeeeeeee 8,8-eeeeeee eeeeeeeee.[‌8‌] Meeee eeeeeee eeeeeee eee eeeeeeeee α-eeeeee eeeee eeeee eeeeeeee eeee eeee eeeeeeeee (‌Meeeee 8‌), eee eeeeeeeee eee-eeeeeeeeeee eeeeeeeee ee ee eeeeeeeeeeee eeeeeee eeee eeeeee eeeee eeeeee (M = M, α-eeeeeeeeeeeee), α-eeeeeeeeeeeeeeeeeeee (M = MeM88, eeeeeeeeeeeeeee), ee 8-eeeeee-8-eeeeeeeeeee (M = Me ee M, eeeeeee–eeeeeee eeeeeeee).

MMMMMM: α-Meeeee eeeee eeeee eeeeeeee, ee eeeeeeeee ee eeeeeee eeeeeeee, eeeee eeeeeeeee eeee eeeee. Me eee eeeeeeeeee eeeee eeeee eeee eee eeeeee eeeeeeeeee eee eeeee eeeeeeeeeee eeee eeeeeeeeeee eeeeee. Meeeeeeeeee eeeeeeee ee eeeee eeeeeeee ee eee eeeeeeeeee eeee ee eeeee eeeeee eeeeeeeee, eeeeeee, eee eeeeeeee ee eeeee eeeeeee eeeee.

References

Meeeeee Meeeeeeeeee

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