Amino diazoacetoacetates 4a-e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c-e furnished the morpholin-2-ones 5c-e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivit
Stereoselective Formation and Rearrangement of Morpholinium Ylides Derived from Copper Carbenoids.
โ Scribed by Kevin W. Glaeske; B. N. Naidu; F. G. West
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 110 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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๐ SIMILAR VOLUMES
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
Allyi aryl sulfides and diazoacetic acid esters react in the presence of optically active Co(lll)salen complex (4) with good enantioselectivity, to give the [2,31sigmatropic rearrangement products, 2arylthio-3-aryl-4-pentenoic acid esters, via the corresponding S-ylides.