Related Experiment Video
Updated: Aug 16, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Silatropic carbonyl ene cyclizations in the synthesis of pseudosugars and hydroxylated piperidines
Jeremy Robertson1, Petra M Stafford, Stephen J Bell
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom. jeremy.robertson@chem.ox.ac.uk
Abstract:
[reaction: see text] We describe two applications of silicon-tethered thermal allyl transfer reactions of alpha-silyloxyaldehydes; formally, these processes can be regarded as silatropic carbonyl ene reactions in which the silicon tether is transferred to the aldehyde oxygen concurrent with carbonyl allylation. In the first application, isoserinal substrates, which bear side-chain nitrogen functionality, are elaborated to dihydroxypiperidines. In the second application, a product of cyclohexadienyl transfer is taken on to carbocylic analogues of, for example, mannose. In both series, the silatropic ene reactions are effected thermally, with no added Lewis acid, and are both stereospecific and highly stereoselective.
More Related Videos
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Biosynthesis of Polysaccharides
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Types of Enols and Enolates
Stereochemical Effects of Enolization

