A remarkable temperature effect in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with chiral oxazolidin-2-ones†
Abstract
A temperature dependent reversal of diastereoselectivity was observed in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with lithiated chiral oxazolidin-2-ones that appears to be kinetically driven at low temperature while the reversibility of the reaction sets in at higher temperatures and thermodynamics governs the reaction outcome.