Science of Synthesis

Heaney, H.; Christie, S., Science of Synthesis, (2004) 3, 588.

As highlighted in the introduction, and in previous sections, cuprates often show different reactivities from copper-catalyzed or organocopper reactions. The main drawback is, however, that 2 equivalents of a particular organometallic reagent are required to produce the cuprate, and only one is transferred to the organic fragment. The second is simply lost on workup. In many cases this may not be an issue, since a lot of reactions will involve the use of, for example, methyl- or butyllithium, which are readily available, commercial starting materials. However, if several steps are required to build a more elaborate system, 50% of this valuable precursor is destroyed.

Mee ee eee eeeeeee eeeeeee eee eee eee ee eeeeee(M) eeeeeee eee eeee eee eeeee eeeee eeeee eee ee e eeeeeeeeeeeeeee eeeeee ee eeeeee eeeeeee eeeeeee eeee eee eeeeeeee ee 8 eeeeeeeeee ee eeeeeeeeeeee. Meeee eeeeeeee eee ee eee eee eeee eeee eeeeeeeeeee ee eeeeeeeeeee eeeeee eeeeeeeeee eeee eeeeeee; eeeeeee, eeee eee eeeeeeeee eeee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeee eeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee ee eee eeeeee(M) eeeeeee. Me ee eeeeeeee ee eeee eee eeeeeeeee eeeeeee (ee eeeee eeeee) eeeeeeee eee ee eee eeeeee, eeee eeeeeeeeee e eeeee eeeeeee. Mee eeeeeee eeeeeee eeee eeee eeeeeeeee eeeeeeeeee eee eee eeeee eeeeee eeee e eeeeee eee ee eeeeeeee eeee eeee eee eeeeee eeeee ee eeeeeeeeeee ee eeeeeeeeee ee eeeeeee. Me eeeeeeeeeeee eee eeeeee eee eeee eeeeeee eee eeeee eeeeeeee ee 8888 ee Meeeeeeee.[‌8888‌] Me-eeeee eeeeeee eeeeeeeeeeee eeeeeee ee eeeeeee eeee eeeeeeeee eeeeeee ee eee eeee ee eeeeee eeee eeeee ee eeeeeeee ee eee eeeeeeee eeeeeee.[‌888‌,‌8888‌,‌8888‌] Me eee eeeee eeeeee eeeeeeeeee, e eeeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeee ee 8 eeeeeeeeee ee eeeeeeeeeeeee eee eeee 8 eeeeeeeeee ee eeeeeeeeeeee ee eeeeee(M) eeeeeee. Meee eee eeeeeeee ee eeee eee eeeeeee eeeee eeeeeee, Me(Me)MeMe•MeMM. Meeeeeee ee eeee ee ee eeeeeee eee eeee eeeeeeeee ee eeeee ee eeeeee ee eeeee eeeee ee e eeeeeeeeee eee eee eeeee ee eee eeeee ee eeeeee eee eeeeeee. Mee eeeeeeee (‌888‌ eee ‌888‌) eeee eeeee, eeeee eeeee eeee eeeeee ee eeee ee eee eeeee eeeeeeeeeeee; eeeeeee, eeeee eee e eeeeeeee eeeeeeeeee eee eee eeeee-eeeeeeeeeee eeeeeee, ee eeeeeeeeeee ee eee 8:8 eeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeee ee e Meeee Meeeeeeeeeee ee ee Meeeeee[‌888‌]

Me eee eeeeeeeeee ee eeee eeeee eeee eee eeeeee eeeeeeeee eeee eeee eeeeeee eeeeeeee ee eee eeeee eeeee eeeeee ee ee eeeeeeeeeee eeeeeeee. Mee eeeeeeee, ee eee eeeee eeeee eeeeeeeeeee, eee eeeeee-eeeeeeeeee eeeeeeeee eeeee ee MeMeMMMe. Meee ee e “eeeee eeeee” eeeeeeeeeeee, eee eeeee eeee eeeeeeeeeee ee eee eeeeeeee. Meeeeee, eeeeeeeee ee eeee eeeeeeeee eeeeeeeeeeee eee eeeeeeee ee eee eeeeeee eeee eeee eeeee eeeeeee ee eee eeeeeeee eeeeeee eeeee eee eeee eeeeeeee eeeeeeeeee. Meee eeee eeeeeeee eee eeeeeeee eeeeeeeeeeee ee eee “eeeeee” eee “eeeee” eeeeeeeeeeeee, eeeeee ee eeeeeeee ee eee ee eee eeeee eeeee, eeeeeeeeeeee. Meee ee eeeeeee eeeee eee ee eee eeeeeeee eeeee eeee eeee ee eeeeeeeeee ee eee eeee eee(eeeee)eeeeeee eee eeeee ee eee eeeeeee. Mee eeeeee eeee eeeeeee eeee ee eeeee eeeeee eeee e eeee eeeeeeeeee, eeeee eeeeeeeee ee eee eeee eeee eeee eee ee eee eee eeeeeeee eeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeeee.

Meeeeee eeee eeeeee eeee eee eeeee eeeeee ee eee eeeeeeee eeee eee(eeeeee)eeeeeeeeeeeee eeeee eeeeeeeeeee.[‌8888‌] Mee eee eeeeeeee Me8MeMe•MeMM eee Me8MeMe•MeMM eeee eeee eeeeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeee eeeee ee eee eeee eeeee. Meeeeeeeee eeeeeeee ee eee eeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeee eee eeeeeeee eeeeeeee ee ‌Meeeee 888‌. Mee eeeeeeeeeeee ee eeeeeeee eee eeeeeeeee eeeeeeeee ee eeee eeeeeeee eeee eee eeeee eeeeeeeeeeee eee eeee eeeeeee ee eeeeeee eeeeeeee. Meee eeeeeeee eeee eee eeeee eeeeee eee ee eeeeeeeee eeee eee eeeeee eeeeee ee eeeeeee eeeee eee eeeeeeee eeeeeeeeee.

M eeeeeeeeeeee eeeeeeeeee eeeeeee ee eee eeeeeee ee eeeeeeee eee eeeee eeeee eeee eee eeeee ee eeeee ee ‌Meeeee 888‌. Meee eee eeee eeeeeee eeee-eeeee eeeee eeeeeee eee eeeeeeeee eeeeeeee ee eee β-eeeeeee, eeeeeeeee eee α-eeeee eeee ee eeeeeeeeee eeeee.[‌888‌]

‌Meeeee 888‌ Meeeeee ee e β-Meeeeee ee Meeeeeee ee e eeee-Meeee Meeee eeee e Meeee Meeeeeeeeeee[‌888‌]

Mee eeeeeee ee eee eeeeee eeeee ee eee ee eee eeeeeeee eeeeee eeeeeee ee ee eeeeeeee ee eeeee eeeee eee eeeee eeeeee eeeeeee ee eeeeeee eeeee eeeee. Meee eeeee ee eeee, eee eeeeeee Me(eeeee)MeMe•MeMM eeeeeeeeeeeeee eeeeee eeeeeee eee eeeeee eeeee ee eeeeeeee eeee e eeeeeeeee eeeeeeee ee ee eeeeeee.[‌888‌] Mee eeee ee eee eeeeeeeeee eeee eeeeeee ee eeee ee eeeeee ee eee eeeeeeee. Me eee eeeeeeeeeeee eee eee Meeeeeee eeeeeee eee eeee ee eeeeee eee eeeee eeeeeeeeeeee, eee eeeee ee eee eeeeeee eee ee eeeeeeee eeeeeeeeeee, eee eeeeee eeeeeeee eeeeeeee ee eeeeeeee. Meee eee eeeeeeee ee eeeeee eeeeeee ee eee eeee ee eeeeeee eeeeeee eeee eee eee eee eeeeeeee.[‌888‌]

Meee eeeee ee eeeeeeeee eeee eee eeeeeeee eee eeeeee ee eee eeeee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee, eee eeeeeeeee eeeeeeee eeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee.[‌8888‌] Meee, eeeeeeee ee eee eeeee eeeee eeeeeee Me(Me)MeMe•MeMM eeeee e eeeeeeeeee eee eeeeeeee ee eee eeeee eeeee ee eeeeeeeeeeeee eee eeeeeeeeeeeeee. Meee eeeeeee, eee eeeeeee Me(eeeee)MeMe•MeMM eeee eeeeeeeee eee eeeee eeeee ee eeeeeeeeee ee eee eeeeee eeeee, eeee ee ee eeeee eeeeeee eeeeeeeeeee ee eee β-eeeeeeee. Mee eeeeee ee eeeee eeeeeeeee eee eeee eeeeeeeee.

Meeeeeee eee eee ee eeeee eeeeeeeeeeeeeeeeeee eee eeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee, eeeee eee eeeee e eeeeee ee eeeeeee eee eeeeeeeeeee eeeee, eee eeee eee eeeeee eee e eeeeeee “eeeee” eeeeee eeeeeeeee. Mee eeee eeeeeeeeee ee eeeee eee eeeeeeeee ee eeee eeeeee eeeee.

MMMMMM: Meeeeee eeeee eee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee. Meee eeeee eeeeee(M) eeeeeee, eeeeee eeeeeeeeee eeeeee ee eeeeeee ee eee eeeee, ee eeeeeee eeeeeeeee ee eeeeeeee eeeeeee.

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeee-8-ee (‌888‌) eee 8-Meeeeeeeeee-8-ee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeeee eeeee eeeee eeeee eeeee eee eeeee MeMM (88.8 ee, 8.8 eeee), eeeeeeeeee eeeee ee eeeeeeeeee eeeeeeeeeeee eeee eeeeeee. Mee MMM (8 eM) eee eeeee eee eee eeeeeeeee eeeeee eeeeee ee −88°M. M 8.88 M eeee ee MeMe ee MMM (888 eM, 8.8 eeee) eee eeeee eeeeeeee, ee eeeeeee e eeeeee eeee. M 8.8 M eeee ee MeMe ee MMM (8.8 eM, 8.8 eeee) eee eeee eeeee. Meee eeeeeeee eeeeee eeeeee ee eee eeeee ee eee eeee. Mee eeeeeeee eee eeeeee ee −88°M eee eee eeeeeee (88 μM, 8.8 eeee) eee eeeee eeee eee e eeeeeee. Meeee 8 e eee eeeeeeee eee eeeeeeee eeee 88% eee. MM8Me/88% eeeee MM8MM eeee (8 eM). Mee eeeeeeee eee eeeeeee eee 88 eee, eeee eeeeeeeee eeee Me8M. MMM eeeeeeee eeeeee eee eeeeeeee eeeeeee ee eeeeee ee 88 eee 8%, eeee 88% eeeeeeee eeeeeeee eeeeeeeee.

References