The first example of enantioselective carbenoid addition to organochalcogen atoms: application to [2,3]sigmatropic rearrangement of allylic chalcogen ylides
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 12,p. 1245-1246
- https://doi.org/10.1039/c39950001245
Abstract
In the presence of a catalytic amount of chiral copper(I) or rhodium(II) compounds the enantioselective addition of a carbenoid, derived from ethyl diazoacetate, to chalcogen atoms of aryl cinnamyl chalcogenides affords a diastereoisomeric mixture of ethyl 2-arylchalcogeno-3-phenylpent-4-enoates via[2,3]sigmatropic rearrangement of the intermediate chalcogen ylide with up to 41% ee.Keywords
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