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Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes

Bin Wang, Dhika Aditya Gandamana, David Fabian León Rayo, Fabien Gagosz* and Shunsuke Chiba*

*University of Ottawa, K1N 6N5, Ottawa, Canada; Nanyang Technological University, Singapore 637371, Singapore, Email: fgagoszuottawa.ca, shunsukentu.edu.sg

B. Wang, D. A. Gandamana, D. F. L. Rayo, F. Gagosz, S. Chiba, Org. Lett., 2019, 21, 9179-9182.

DOI: 10.1021/acs.orglett.9b03548 (free Supporting Information)


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Abstract

Electrophilic bromination or fluorination of homoallylic alcohol O-Bn ethers triggers a diastereoselective hydride transfer to provide diastereomerically enriched haloalkyl alcohols. A subsequent intramolecular nucleophilic substitution affords tetrahydrofurans.

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Key Words

Tetrahydrofurans, Selectfluor


ID: J54-Y2019