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Direct observation of the formation and rearrangement of carbene/allyl sulfide ylides

✍ Scribed by Moss, Robert A.; Ho, Guo Jie; Sierakowski, Claudia


Book ID
126117857
Publisher
American Chemical Society
Year
1992
Tongue
English
Weight
305 KB
Volume
114
Category
Article
ISSN
0002-7863

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Trimethylsilyldiazomethane is compared with ethyl diazoacetate for the rhodium, copper, and cobalt catalyzed formation and [2,3] rearrangement of allylsulfonium ylides. At room temperature, the reaction can be carried out using the allyl sulfide as the limiting reagent by slow addition of 3 equivale

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The tandem sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic secondary allylic sulfides, (E)-9 and (Z)-10, is found to proceed with high diastereocontrol. The C-5 stereocenter bearing the sulfide group is essential for high diastereoselectivity in the reaction.