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2004
Cyclopentane derivatives
Q 0030
Catalytic Asymmetric Intramolecular Michael Reaction of Aldehydes. — Chiral
chloride IMI efficiently catalyzes the cyclization of formyl enones (I)
45- 077 imidazolidinium
or (III) to provide cyclic ketoaldehydes in excellent yields, with high diastereo- and enantioselectivities, and under mild and convenient reaction conditions. The process is
applied for the syntheses of hydrindenone (IV) and diketone (VI) in high yields and
enantiomeric purity from aldehyde (III). It involves the in situ intramolecular aldolization of the ketoaldehyde derived from enone (III), and a
Horner—Wadsworth—Emmons reaction with phosphonate (V). — (HECHAVARRIA
FONSECA, M. T.; LIST*, B.; Angew. Chem., Int. Ed. 43 (2004) 30, 3958-3960; MPI
Kohlenforsch., D-45470 Muelheim/Ruhr, Germany; Eng.) — Klein
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