An efficient synthesis of optically active 4-methyloxetan-2-one: asymmetric hydrogenation of diketene catalysed by binap–ruthenium(II) complexes [binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]

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Abstract
Highly enantioselective hydrogenation of diketene with the catalytic system derived from {RuCl[(S)- or (R)-binap](benzene)}Cl and triethylamine or with Ru2Cl4[(S)- or (R)-binap]2(NEt3)[binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] in tetrahydrofuran gives optically active 4-methyloxetan-2-one in up to 97% selectivity and 92% enantiomeric excess (e.e.).