1997 cyclohexane derivatives

cyclohexane derivativesQ 0040

01 - 1041,3-Dienylboronates in Diels-Alder Reactions. Part 2. — Diels-Alderreaction of the achiral boronate (I) and methylacrylate ( II) followed by allylb-oration of the resulting diastereomeric mixture and final silylation provides theester (VII) as the same mixture of diastereomers, in agreement with a fullycontrolled reaction of intermediate allylboronate in the presence of an aldehyde.Performing the same tandem sequence on enantiomerically pure (VIII) providesthe major diastereomer in 70% e.e. — (RENARD, P.-Y.; LALLEMAND,J.-Y.; Tetrahedron: Asymmetry 7 (1996) 9, 2523-2524; Lab. Synth. Org., Ec.Polytech., F-91128 Palaiseau, Fr.; EN)

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