Treatment of the racemic disubstituted pent-4-enals (1) and (2) at ca. 150 °C with the chiral complex [Rh(chiraphos)2]Cl [chiraphos = 2S,3S-bis(diphenylphosphino)butane] results in a cyclisation reaction and catalytic asymmetric synthesis of the 2,2- and 3,3-disubstituted cyclopentanones (3) and (4), respectively.
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James et al. (1983) studied this question.