Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene p...

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Bibliographic Details
Main Authors: Morifumi Fujita, Koki Miura, Takashi Sugimura
Format: Article
Language:English
Published: Beilstein-Institut 2018-03-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
1,2-difunctionalization of alkenes
enantioselective synthesis
hypervalent iodine
oxidation
Online Access:https://doi.org/10.3762/bjoc.14.53
Description
Summary:A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene proceeded with high enantioface selectivity to give 1-aryl-1,2-di(tosyloxy)ethane with an enantiomeric excess of 70–96% of the (S)-isomer.
ISSN:1860-5397

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