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New and Efficient Chiral Selenium Electrophiles

Uehlin, Lars, Fragale, Gianfranco and Wirth, Thomas 2002. New and Efficient Chiral Selenium Electrophiles. Chemistry - A European Journal 8 (5) , pp. 1125-1133. 10.1002/1521-3765(20020301)8:5<1125::AID-CHEM1125>3.0.CO;2-I

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New chiral diselenides were prepared in a few steps from readily available starting materials. The selenium electrophiles generated from these diselenides were used for the efficient stereoselective inter- and intramolecular functionalization of alkenes. The substitution pattern influences the stereoselectivities and protection of the hydroxy moiety in the chiral side chain led to increased selectivities and yields in the selenenylation reactions. An additional substituent in the second ortho position was advantageous as well. Addition products with up to 96 % de were obtained. The influence of the nucleophile on the outcome of selenenylations of alkenes was studied to some extent as well.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: alkenes; electrophiles; heterocycles; selenium; stereoselective synthesis
Publisher: Wiley-Blackwell
ISSN: 1521-3765
Last Modified: 04 Jun 2017 01:39

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