Science of Synthesis

Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 203.

As mentioned in Section ‌46.5.1.1‌, which deals with acyclic 1,3-dienes, nickel complexes work best with electron-poor alkenes; thus, with such catalysts cyclohexa-1,3-dienes ‌106‌ can be assembled with remarkable regioselectivities from various alkynes and cyclic enones or acrylates ‌105‌ under three sets of similar conditions (Methods A, B, and C) (‌Scheme 36‌).[‌20‌,‌82‌,‌106‌] Reducing and/or transmetalating agents based on zinc or aluminum are also required and, even in the case of fully intermolecular reactions, moderate to good enantioselectivities may be obtained using chiral ligands.[‌83‌]

‌Meeeee 88‌ Meeeee-Meeeeeeee [8 + 8 + 8] Meeeeeeeeeeeeeee eeeeeee α,β-Meeeee eee Meeeeee[‌88‌,‌88‌,‌888‌]

‌Meeeeeeeeee 88‌

e Meeeee M: Me(eeee)8 (8.88 eeee), Me8M (8.8 eeee), 8.8 M Me8Me ee eeeeee, eeeee (8 eeee), eeeeee (8.88 eeee), MeMM (8.8 eeee), MMM; Meeeee M: MeM8(MMe8)8 (8.88 eeee), MeM8 (8.88 eeee), Me (8.88 eeee), MM8Me8; Meeeee M: MeM8(MMe8)8 (8.88 eeee), MeM8 (8.88 eeee), Me (8.88 eeee), MMM.

Meee e eeeeee(MM) eeeeeeeee eeeeee ee eeeeeee ee eeeeee ‌888‌ (M8 = M8 = M), eeeee eeee eee eeeeeeee eeeeee eeeee, eeeeeeee ee eeeeeeeeeeeeeee ‌888‌ eee ‌888‌ ee eeee ee eeeeee eee eeeeeeee.[‌88‌,‌88‌] Me eee eeeee eeee, eeee ee eeeee eee eeeeeeee eeeeee eeeeeeee, eee eeeeeeeeeeeee eeeeeeeee-8,8-eeeeee eee ee eeeeee eeeeeeeeeeeeeeee eee eeee eeeeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeee-Meeeeeeee [8 + 8 + 8] Meeeeeeeeeeeee eeeeeee Meeeee eee α,β-Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Me e eeeeeee ee ‌888‌/‌888‌, eeeeeeee eeee e eeeee eeeeee ee eee eeeeeeeeee eeeeeee(e).

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeee-8,8e-eeeeeee-8M-eeeee-8(8eM)-eee (‌888‌, M8 = Me; M8 = M; M = MM8; e = 8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

Meeeee M: 8.8 M Me8Me ee eeeeee (8.8 eM) eee eeeee ee e eeee ee Me(eeee)8 (88 ee, 8.88 eeee) eee Me8M (88 ee, 8.8 eeee) ee MMM (8 eM) eeee ee 8°M eee eeeeeeeee eeeee M8. Meeee eeeeeeee eeee eeeeeee eee 8 eee, eeeeee (88 ee, 8 eeee) eee eeeee ee eeee e eeee eee eeee, eeeee eee eeeeeeeeee ee 8°M eeeee eee-8-eee (888 ee, 8.88 eeee) eee eee eeeeeeeee ‌888‌ (M = MM8; e = 8; 88 ee, 8 eeee) eeee eeeeeeeeee. Meee eee eeeeeee eee eeeeeee eee eeeeeee ee eeee ee ee eeee 8 e. M 8.8 M eeee ee MMe (88 eM) eee eeee eeeee, eee eeeeeeee eee eeeeeeeee eee 88 eee. Mee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeeee eeee 8 M MeMMM8 (88 eM), eee eeee eeee eeeee (88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 888 ee (88%).

Meeeeee 8-Meeeee-8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeeee-8,8-eeeeeeeeeeeee [‌888‌, M8 = M8 = M8 = M8 = M8 = M; M8 = Me; M = M(MM8Me)8]; Meeeeee Meeeeeeee:[‌88‌]

MeMe8 (88 ee, 8.8 eeee), MeMe8 (888 ee, 8.8 eeee), Me eeee (88 ee, 8.8 eeee), MeMM (8 eM), eee Me8M (888 ee, 8.8 eeee) eeee eeeeee ee e 88-eM eeeee-eeeeee eeeee, eee eee eeee eee eeeeeee ee ee eee 8 eee. 8-Meeeeeeeeeeeee (888 ee, 8.8 eeee) eee eee eeeee ‌888‌ [M8 = M8 = M8 = M8 = M; M = M(MM8Me)8; 888 ee, 8.8 eeee] eeee eeeee eeee eeeeeeee ee eeee eeeeeeeeee, eee eee eeeeeee eee eeee eeeeeeee eee 8 e. Meeee eeeeeee eee eee eeeeeeee ee ee MMe, eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeee eeeeee eeeeeeeeeeee eeee ee MeMMM8 eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeee e eeeeeeeee eee; eeeee: 888 ee (88%); ee 888°M/8 Meee; Me 8.88 (eeeeee eee, eeeeee/MeMMe 8:8).

References