Synthesis and reactions of terpenyl diselenides functionalized with phenyl and naphthyl groups | Health & Environmental Research Online (HERO)

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HERO ID

4668540

Reference Type

Journal Article

Title

Synthesis and reactions of terpenyl diselenides functionalized with phenyl and naphthyl groups

Author(s)

Scianowski, J; Szumera, J; Kiernan, P; Paulla, AJ

Year

2016

Is Peer Reviewed?

Journal

Tetrahedron: Asymmetry
ISSN: 0957-4166

Volume

Issue

Page Numbers

238-245

Language

English

DOI

10.1016/j.tetasy.2016.02.004

Web of Science Id

WOS:000372760700002

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84960415275&doi=10.1016%2fj.tetasy.2016.02.004&partnerID=40&md5=7ca16b1dc7116db74e4a93485e8e460b
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Abstract

An efficient methodology for the synthesis of chiral terpenyl diselenides functionalized with phenyl and naphthyl groups has been developed. Using the reaction of sodium diselenide with terpenyl tosylates and chlorides, the corresponding diselenides derived from 8-phenyl menthol and isopinocampheol modified at the 10-position were obtained. Diselenides were transformed into electrophilic selenium reagents and tested in the asymmetric selenenylation of styrene. The effect of aryl groups on the enantioselectivity of the addition reaction was examined. (C) 2016 Elsevier Ltd. All rights reserved.