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Mase, N., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 155.
Enals, enones, and α,β-unsaturated esters 1 are chemoselectively reduced to the corresponding saturated carbonyl compounds 2 by an octacarbonyldicobalt(0)–water system at reflux (Scheme 2).[8] More convenient and cost-effective reduction of enones and α,β-unsaturated esters 1 is accomplished using a magnesium–zinc(II) chloride system under aqueous conditions, in which exothermic reductions are completed within 1 hour (Scheme 2).[9]
Meeeee 8 Meeee-Meeeeee-Meeeeeee Meeeeeeee Meeeeeeee ee α,β-Meeeeeeeeee Meeeeeee Meeeeeeee[8,8]
M8 | M8 | Meeeeeeeee | Meee (eee) | Meeee (%) | Mee |
---|---|---|---|---|---|
M | Me | Me8(MM)8 (8 eeeee), MMM, M8M (88 eeeee), eeeeee | 888 | 88e | [8] |
Me | Me | Me8(MM)8 (8 eeeee), MMM, M8M (88 eeeee), eeeeee | 888 | 888 | [8] |
MMe | Me | Me8(MM)8 (8 eeeee), MMM, M8M (88 eeeee), eeeeee | 888 | 88 | [8] |
MMe | MM8Me | Me8(MM)8 (8 eeeee), MMM, M8M (88 eeeee), eeeeee | 888 | 88 | [8] |
Me | Me | Me (8.8 eeeee), MeMe8 (8.8 eeeee), M8M | 88 | 88 | [8] |
Me | Me | Me (8.8 eeeee), MeMe8 (8.8 eeeee), M8M | 88 | 88 | [8] |
(MM8)8 | Me (8.8 eeeee), MeMe8 (8.8 eeeee), M8M | 88 | 88 | [8] | |
(MM8)8 | Me (8.8 eeeee), MeMe8 (8.8 eeeee), M8M | 88 | 88 | [8] | |
MMe | Me | Me (8.8 eeeee), MeMe8 (8.8 eeeee), M8M | 88 | 88 | [8] |
e (M)-8-Meeeeeeeee-8-ee-8-ee eee eeee eeeeeeee ee 88% eeeee.
Meeeeeeeeeeee, eeeeeeeee ee eee eeeeeeeeee eeeeee 8 ee eee eeeeeeee ee ee eeeeee ee eee eeeeeeeee–eeee(MM) eeeeeeee eeeeeeee eeee eeeee ee eee eeeeeeeeeeeee eeeeeeeee eeeee 8 ee eeee eeeee (Meeeee 8).[8]
Meeeee 8 Meeeeeeee–Meee(MM) Meeeeeee Meeeeeee Meeeeeeee ee e Meeeeeeeee Meeeee[8]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeee-8-eee (8, M8 = M8 = Me); Meeeeee Meeeeeeee:[8]
Me e eeeeeeeeee ee (M)-8,8-eeeeeeeeeeee-8-ee-8-eee (8, M8 = M8 = Me; 8.88 e, 8 eeee) ee eeeeeeeee M8M (88 eM) eee eeeee Me eeeeeeee (888 ee, 8.8 eeee) eee MeMe8 (8.8 e, 8.8 eeee) eeeee eeeeeeee. Meeeeeeeeee eeeee eeeeeeee ee Me, ee eeeeeeeeee eeeeeeee eeee eeeee (MMMMMMM) eee eee Me eeeeeeee eeee eeeeeeee, eeeeee e eeee, eeeeee eeeeeee. Meeee eeeeeeee eee 88 eee, eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeeeee 8,8-eeeeeeeeeeeeee-8-eee (8, M8 = M8 = Me) ee ee eee-eeeee eeeee; eeeee: 8.88 e (88%).
References
[8] | Mee, M.-M.; Me, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[9] | Meeeee, M.; Meeeeeeee, M. M.; Meeeee, M. M., Meeeeee, (8888), 888. |