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: fgagosz
uottawa.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
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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
ID: J54-Y2019
