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

✍ Scribed by J.Stephen Clark; Mark Fretwell; Gavin A. Whitlock; Christopher J. Burns; David N.A. Fox

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 639 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10441-5

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✦ Synopsis

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 obtainedusing a coppercomplexof the enantiomericatlypure diimine la forcarbenoid generation.

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