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DOI: 10.1055/sos-SD-046-00090

Gandon, V.; Thorimbert, S.; Malacria, M.Science of Synthesis, (200946203.

As mentioned in Section, 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

M e M8 M8 Meeeeee Meeeeeeeee Meeee (%) Mee
MM8 8 Me M M ee, 8e 88 [‌88‌,‌888‌]
MM8 8 Me Me M ee, 8e 88 [‌88‌,‌888‌]
MM8 8 Me M M ee, 8e 88 [‌88‌,‌888‌]
MM8 8 Me M M ee, 8e 88 [‌88‌,‌888‌]
MM8 8 Me Me M 88°M, 88e 88 [‌88‌]
MM8 8 Me Me M 88°M, 88e 88 [‌88‌]
M 8 Me Me M 88e 88 [‌88‌]
M 8 Me Me M 88e 88 [‌88‌]

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

M8 M8 M8 M8 M8 M8 M ee Meeee (%) Mee
M M M M M Me M(MM8Me)8 88 [‌88‌]
MMM M M M Me M M 88 [‌88‌]
Me M M M Me M M 88e [‌88‌]
MMM M M MMMMMM Me M MMe8 ee. 8:8 88 (888) [‌88‌]
MMM M MMMMMM M Me M MMe8 ee. 8:8 88 (888) [‌88‌]
MMM Me MMMMMM M Me M MMe8 ee. 8:8 88 (888) [‌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); MeeeeeeMeeeeeeee:[‌888‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

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

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