Science of Synthesis

Heaney, H.; Christie, S., Science of Synthesis, (2004) 3, 611.

Vinylcuprates are among the most effective reagents for conjugate addition reactions. In general, ethereal solvents, in particular tetrahydrofuran, are used. The reaction is even more efficient when a trapping agent is used (e.g., in the reaction to give ‌125‌), further highlighting the utility of 1,4-addition protocols. The three examples in ‌Scheme 469‌ illustrate how different trapping agents will react through oxygen or carbon, and that functionalized cuprates can be employed.[‌1588‌,‌1589‌]

‌Meeeee 888‌ Meeeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeee Meeeee[‌8888‌,‌8888‌]

Meeeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeee eee ee eeeeeeee ee eee eeeeeeeee. Mee eeeeeeee ee ‌Meeeee 888‌ eeee eeee eeeeee eeeeeeee eee eeeeeeee eeeeeeeeeeeee ee e eeeeee eeeee eee eeee ee eeeeee ee eee eeeeeeeeeeee ee eee eeeeeeee.[‌8888‌]

‌Meeeee 888‌ Meeeeeeeeeeeeeee Meeeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeee Meeeee[‌8888‌]

Mee eee ee eeeeeee eeeeeeeee ee eeeeeee eeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeee eee ee eeee eeeeeeee M—M eeeee ee eeee eeeeeeeeeee ee eeeeeeeee eeeeeeeee (e.e., ee eeee ‌888‌, ‌Meeeee 888‌). Meee, eee eeeeeee eeeeee eeee eee eeeeeee 8,8-eeeeeeee ee eeee ee e eeeeeee eeeee eeeeeeee. Mee eeeeeeeeeeeeeee ee eee eeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeeee.[‌8888‌,‌8888‌]

‌Meeeee 888‌ Meeeeeeee Meeeeeee–Meeee Meeeeeeeeee Meeeeeeee[‌8888‌,‌8888‌]

Meeeeeeee γ-eeeeeee-α,β-eeeeeeeeeee eeeeee eee eeee ee eeeeeeee ee eeeeeee eee eeeeeeeeeeeeeee ee eeeeeeeee eeeeeeeee (‌Meeeee 888‌).[‌8888‌] Mee eeeeeeee eeeee eeeee eeee e eeee eeeeee ee eeee eeeeeeeeeee. Mee eeeeeeee eee eeee ee eeee ee eeeeeee eeeeeeeeeeeeeeee eeeeeeeee, eeeeeeeee e eeeeeeee eeee e eeee eeee eeeee ee eeeeee- eee eeeeeeeeeeee. Meeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee ee eeeee e eeeeeeeeeeeeeee ee e eeeeee eeeeeeeee.[‌8888‌]

‌Meeeee 888‌ Meeeeeeee-Meeeeeeeee Meeeeeeee Meeeeeee ee Meeeeee[‌8888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-(eeeeeeeeeeeeeee)-8-eeeeeeeeeeeeee-8-eee (‌888‌); Meeeeee Meeeeeeee:[‌8888‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee (MMMM) ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

M eeee ee MM8=MMMe (88.8 eM, 8 eee) ee MMM (888 eM) eee eeeee ee Me (8.88 e, 888 eeee) ee MMM (888 eM), eeeeeeeeee ee e eeeeeeeeeee ee 88°M. Meee eee Me eee eeeeeeeeeee eee eeeeeee eee eeeeee ee 88°M eeeee e eeeeee ee M8 ee eeeeee eeeeee MM8=MMMe. Meeee eeeeeee ee −8°M, MeM (88.88 e, 888 eeee) eee eeeee eee eee eeeeeee eeeeeee eeeee eee eeeee; eeee 8-eeeeeeeeeeeeeee-8-eeeee (88.88 e, 888 eeee) ee MMM (88 eM) eee eeeee eeeeeeee eee eee eeeeeee eeeeeee eee 88 eee ee −88°M. MMMMe (88 eM, 888 eeee), MMMM (88 eM), eee Me8M (88 eM) eeee eee eeeee eeeeeeeeeeee eeeee eeeeeee ee −88°M; eee eeeeeee eee eeee eeeeeee ee eeee ee ee eeee 8 e. Me eeeeeee eeeeeeeee eeeee eeeeee, eeeeeeee ee eeeeeeeeeeee, eeee ‌888‌ ee e eeeeeeeee eee; eeeee: 88.88 e (88%); ee 88–88°M/8 Meee.

(8M,8M,8M)-8-[(8M)-8-Meeeeeeeee-8-eeee]-8-eeeeeeeeeee-8-eeeeeeeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌8888‌]

MM8=MMMeMe (8 eeeee) eee eeeee ee MeMe (8 eeeee) ee Me8M eee eee eeeeeee eeee (M)-(–)-8-eeeeeeeeeeeeeeeeeee-8-eeeee. Mee eeee eee eeeeeee eee 88–88 eee ee −88 ee −88°M eee e eee. eeee ee MeMe8 (8–8 eeeee) ee Me8M eee eeeee, eeeeeeee ee e 8- ee 8-eeee eeeeee ee eeeeeeeeeeeeee [(8M)-eee-8-eeee]. Meeee eeeeeeee eee 88 eee, eee eeeeeee eee eeeeeeee eeee ee eeeeee ee 88% MM8Me (eM 8) eee eee eeeeeee eeeee eeeeeeeee. Mee eeeeeee eeeee eee eeee eeeeeeeee eeee Me8M (8 ×) eee eee eeeeeeee eeeeeee eeeeee eeeeee eeee 88% MM8Me (eM 8), M8M, eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee ee eeee eee eeeeeeee β-eeeeeee eeeeeee (<88%); eeeeeeee eeeee: 88%. Meeeeeeeee ee MMMM (eeeeee eee) eeee eee eeee eeeeeee ee eeeeeeeee eeee (β-‌888‌, 88%; α-‌888‌, 88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.