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ChemInform Abstract: Asymmetric Methoxyselenenylation of Alkenes with Chiral Ferrocenylselenium Reagents.

✍ Scribed by S. FUKUZAWA; K. TAKAHASHI; H. KATO; H. YAMAZAKI


Publisher
John Wiley and Sons
Year
2010
Weight
41 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


1998 organo-selenium compounds, isocyclic C derivatives organo-selenium compounds, isocyclic C derivatives S 0134 15 -187 Asymmetric Methoxyselenenylation of Alkenes with Chiral Ferrocenylselenium Reagents.

-Best results are observed using the ferrocenylselenium compound shown in the scheme. From cycloalkenes trans adducts are obtained with good selectivity, while from cis-2-butene the erythro adduct is formed with moderate selectivity. trans-2-Butene gives the threo product with high selectivity (exact configuration is not determined). The reaction with silyl enol ethers yields Ξ±-seleno ketones with moderate to excellent diastereoselectivity. In the presence of the chiral diselenide and (NH 4 ) 2 S 2 O 8 alkenes like (XI) are converted into enols such as (XII) in low optical yields.


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