Science of Synthesis

Hodgson, D. M.; Humphreys, P. G., Science of Synthesis, (2008) 36, 606.

The most widely known method for the 1,2-reduction of an α,β-unsaturated ketone uses sodium borohydride and cerium(III) chloride in methanol (Luche reduction).[‌117‌] Under these conditions, the selective reduction of the enone chromophore may now occur even in the presence of an aldehyde group.[‌118‌] This contrasts with reductions using sodium borohydride in the absence of a lanthanide salt, which are typically unselective and form some of the corresponding alcohol and the saturated ketone by 1,4-addition of hydrogen. The presence of erbium(III) trichloride as the additive allows the selective reduction of α,β-unsaturated aldehydes in the presence of a nonconjugated aldehyde function.[‌119‌] Luche reactions can also be run in aqueous media and, in certain cases, this results in increased rates of reaction relative to those carried out in methanol.[‌120‌]

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‌Meeeee 88‌ 8,8-Meeeeeeee ee α,β-Meeeeeeeeee Meeeeeee Meeeeeeee eeee Meeeeee Meeeeeeeeeeeeeeee[‌888‌]

Meeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeeee, eeeeeeeee eeeeeeeeeeee ee M-, MM-, M-, eee MM-Meeeeeeeeee, eee eeee eeeeee eee eee eeeeeeeee eeeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee.[‌888‌,‌888‌] Meee, eee eeeeee ee eeeeeeeee eeeeee eeeeee ee eee eeeeee ee eeeeeeeee eeeee eeeeee ee eee eeeeeeeeeee eeeeee eeeeee eee ee eeeeeee eeeeeee ee eeeee- eee eeeeeeeeeeeeeeeeeeee.[‌888‌] Mee ee eeeee eeeeeee eee eeeeeeeee eeeeeeeeeeee eee ee eeeeeeee ee eeeeee eeeeeeeeeeee ee eee Meeee eeeeeeeee ee eeee eee eeeeeeeeeeee eee eeeeeeeee eeee ee Meeeee–Mee eeeeeeeeeeeeeee ee eee eeeeeee eeeeeeee eeee eee eeeeeeee, eee eee eeeeee ee eee eeeeeee eee eeee ee eeeeee ee eee eeeeeee eeeeeeeeeeee.[‌888‌] Meeee eeeee eeeeeeee eeeeee eee eeee eeeeeeeeee eee eee eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee; eeee, eeee eeeeeeeeeee eee ee eeee ee eeeeee α,β-eeeeeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeee ee eeeeee.[‌888‌,‌888‌] Meeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee ee −88°M ee eeeeeee eeeeeeeee eeeeeee eee eee 8,8-eeeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee eee eeeee eeee ee eeeeeeeee eeeeee.[‌888‌] Meee eeee eeeeeeee eeeee ee eeeeee eeeeeeee ee eeee ee eeeeeeee eeeeeeeeeeeeeeeeeeee(MM) eeeeeeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

(8M,8M)-(–)-eee-Meeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

8 M Meeeeee eeeeeeeeee-8-eeeeeeeeeeeee ee MMM (88 eM, 88 eeee) eee eeeee eeeeee ee e eeeeeee eeee ee (M)-(–)-eeeeeee (‌88‌; 8.8 e, 8.8 eM, 88 eeee) ee MMM (88 eM) ee ee eee eeee ee eee eee. Meeee eeeeeeee eee eeeeeee eee 8 e, ee eee eeeeee ee 8°M eee M8M (8 eM) eee eeeee, eeeeeeee ee 8 M MMe (88 eM, 88 eeee). Mee eeeeeee eeeee eee eeeeee eeee Me8M (8 × 88 eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee. Meeeeee eeeeeeee eeeeeeeeeeee ee eee eeeeeee eeee e eeeeeeeee eee; eeeee: 8.88 e (88%); ee 88–88°M/8.8 Meee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.