Rhodium (II) acetate catalysed decomposition of the diazo sulphoxides (1) and ( 3) gives the cyclic sulphoxonium ylides ( 2) and ( 4); the structures of ( 2~) and (4a) were confirmed by X-ray crystallography.
Rhodium carbenoid mediated cyclisations. Synthesis and rearrangement of cyclic sulphonium ylides
โ Scribed by Christopher J. Moody; Roger J. Taylor
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 216 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
## Sumnary: Treatment of the diazo-compounds (31, obtained in two steps from readily available hydrazine derivatives (11, with a catalytic amount of rhodium (II) acetate
Copper carbenoids undergo efficient intramolecular insertion into ally1 ethers, and 'the resulting ylide-type species rearrange to furnish cyclic ethers (ring sizes 6-8) in high yield. Copper(E) hexafluoroacetylacetonate is an extremely efficient catalyst for this reaction, and use of this complex
Tetmhydrofumn-3-ones and tetrahydropymrr-3-ones can be prepmedenrmtiosekxtively by rearrangementof the ylide-typeintermediatesgeneratedby the reactionof a chiral copper carbenoidwith the oxygenatom of a pendant allylic ether. Cyclic ethers with enantiomericexcesses of up to 57% have been obtainedusi