Stereo- and Regioselective Synthesis of Cyclic Ethers by Means of Organoselenium- Mediated Cyclization of Unsaturated Alcohols

Author(s): Zorica M. Bugarcic , Marina D. Kostic , Vera M. Divac .

Journal Name: Current Organic Chemistry

Volume 20 , Issue 7 , 2016

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Abstract:

In the past several decades, significant progress has been made in the exploration of cyclofunctionalization reactions promoted by electrophilic organoselenium reagents. Numerous natural and biologically active products have been prepared by using this synthetic route. Increased research interest in this topic brings several relevant reviews, which cover wide scope of selenium-induced heterocyclizations. The reaction of electrophile selenium- induced cyclization of alkenes bearing suitable oriented hydroxyl group (termed selenoetherification) present useful tool for the preparation of different cyclic ethers units, which are the key structural units of many natural products. The coverage of this review will be limited to the examples of stereoselective and regioselective synthesis of five- and six-membered cyclic ethers by means of selenium-induced cyclization of unsaturated alcohols. The influence of some Lewis acids and bases, as additives, on regioselection of selenoetherification reaction will be also discussed.

Keywords: Unsaturated alcohols, organoselenium reagents, cyclic ethers, cyclization, asymmetric synthesis, regioselective synthesis.

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Article Details

VOLUME: 20
ISSUE: 7
Year: 2016
Page: [777 - 797]
Pages: 21
DOI: 10.2174/1385272819666150917011909
Price: $58

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