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Synthesis of cyclic ethers from copper carbenoids by formation and rearrangement of oxonium ylides

โœ Scribed by J.Stephen Clark; Steven A. Krowiak; Leslie J. Street

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
286 KB
Volume
34
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 minim&s competing C-H insertion.

๐Ÿ“œ SIMILAR VOLUMES

Asymmetric Synthesis of Cyclic Ethers by
Asymmetric Synthesis of Cyclic Ethers by Rearrangement of Oxonium Ylides Generated from Chiral Copper Carbenoids
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

Stereoselective formation and rearrangem
Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids
โœ Kevin W. Glaeske; B.N. Naidu; F.G. West ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 153 KB

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