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Rhodium carbenoid mediated cyclisations. Synthesis and rearrangement of cyclic sulphonium ylides

โœ 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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๐Ÿ“œ SIMILAR VOLUMES


Rhodium carbenoid mediated cyclisations.
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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.

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## 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

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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

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โœ J.Stephen Clark; Mark Fretwell; Gavin A. Whitlock; Christopher J. Burns; David N ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 639 KB

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