Abstract
Asymmetric transfer hydrogenation of cyclic enones results in highly enantioselective reduction to cyclic allylic alcohols.
Key words
asymmetric catalysis - enones - enantioselective hydrogen transfer - regioselectivity - ruthenium
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13 The unsaturated ketone 3a was prepared by allylic oxidation of 1-phenylcyclohex-2-ene using a 1:1 molar combination of tert -butyl hydroperoxide and pyridinium dichromate.
[6
14 1,2-cyclohexanedione was treated with benzyloxytri-methysilane to afford diosphenol ether 3b
[7 3c
8 3 with R = t -Bu was obtained by addition of t -BuLi to 7-oxabi-cyclo[4.1.0]heptan-2-one, followed by water elimination.
[11
15 Ketone 5 was prepared by radical addition of N -chloro-carbamate to 1-methoxycyclohexene;
[10 4c was obtained by reduction of 3c with sodium borohydride and cerium chloride. The acyclic enone 8 was synthesised in 2 steps starting from the commercially available 3-chloro-butan-2-one via 3-azidobutan-2-one.
[12
16 Acyclic enones 7 and 8 were reduced under the same conditions as displayed in Schemes
[1 2 3a -c .
