Solid-phase asymmetric synthesis using a polymer-supported chiral Evans'-type oxazolidin-2-one
作者： Rachel Green , Jennifer Peed , James E Taylor , Richard A R Blackburn , Steven D Bull
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摘要: This protocol describes the synthesis of (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one, its attachment to a Merrifield-Cl resin and use for asymmetric synthesis. The chiral auxiliary is prepared in four steps from N-Boc-L-tyrosine on multigram scale high yield attached via phenolic group afford solid-supported that takes ∼7 d prepare. A procedure N-acylation reported method carrying out diastereoselective Evans' syn-aldol reactions described, with aldol products being cleaved polymer by either hydrolysis or reduction. supported two sequential 'on-bead' has been demonstrated cyclopropane γ-lactone >95:5 diastereomeric ratio. These polymer-supported are carried IRORI Kan capsules protect support mechanical degradation, thus allowing multiple on-bead be performed.
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