1977
DOI: 10.1021/jo00432a007
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Asymmetric reduction of acetophenone with lithium aluminum hydride complexes of terpenic glycols

Abstract: Optically active 1,2-glycols derived from (+)-l-menthene, (-f-)-a-terpineol, and ( + )-«-and (-)-d-pinene formed chiral complexes with lithium aluminum hydride. The complexes were used to reduce acetophenone in different solvents and at various temperatures. The solvents included dioxane, diethyl ether, ethylene glycol dimethyl ether, and tetrahydrofuran, and temperatures ranged from -50 to 66 °C. Enantiomeric excess was maximum when the solvent was diethyl ether and the temperature was 15-20 °C. Various glyco… Show more

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Cited by 18 publications
(1 citation statement)
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“…The facial selectivities realized in the LAH reduction of aromatic methyl ketones using modifier 10b are superior to those utilizing simple terpenic diol modifiers (<30% ee) . Our results demonstrated the importance of the anilino substituent at C-10 in the modifier 10b , compared with the N -methylanilino substituent of 11 or the benzyloxy substituent of 12 , for the control of chirality in the enantioselective LAH reduction of ketones.…”
Section: Resultsmentioning
confidence: 75%
“…The facial selectivities realized in the LAH reduction of aromatic methyl ketones using modifier 10b are superior to those utilizing simple terpenic diol modifiers (<30% ee) . Our results demonstrated the importance of the anilino substituent at C-10 in the modifier 10b , compared with the N -methylanilino substituent of 11 or the benzyloxy substituent of 12 , for the control of chirality in the enantioselective LAH reduction of ketones.…”
Section: Resultsmentioning
confidence: 75%