Potassium Hydroxide → (2R,4R)-4-cyclohexyl-1,2,3,4-tetrahydronaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

(Peach, P, Cross D J, Kenny J A, Mann I, Houson I, Campbell L, Walsgrove T, and Wills M (2006) Asymmetric transfer hydrogenation of a,3-unsaturated, a-tosyloxy and a-substituted ketones. Tetrahedron 62:1864-1876), (Alcock N J, Mann I, Peach P, and Wills M (2002) Dynamic kinetic resolution-asymmetric transfer hydrogenation of 1-aryl-substituted cyclic ketones. Tetrahedron:Asymmetry 13:2485-2490), (Mogi M, Fuji K, and Node M (2004) Asymmetric reduction of methoxy substituted 3-tetralones using transfer hydrogenation. Tetrahedron:Asymmetry 15:3715-3717) Benzeneruthenium(II) chloride dimer (55 mg, 0.11 mmol) and (1R,2R)-(−)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine (80 mg, 11 mmol) were mixed in iso-propanol (25 mL) and heated at 80° C. for 30 min, to generate the catalyst mixture. Separately, 4-cyclohexyl-3,4-dihydronaphthalen-2-yl phenylacetate 1a (950 mg, 2.8 mmol) was heated to 50° C. in iso-propanol (25 mL). Nitrogen gas was used to push the catalyst mixture through a double ended needle to the flask containing 1a, directly followed by a mixture of KOH (0.5 g) in iso-propanol (50 mL). After 3 hours, the reaction was filtered through a pad of silica gel on Celite and then concentrated under reduced pressure. The crude material was purified by column chromatography (Si-gel) to give 2a in a 40% yield.

Provenance & Evidence