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J Org Chem. 2018 Feb 2;83(3):1312-1319. doi: 10.1021/acs.joc.7b02587. Epub 2018 Jan 22.

Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline.

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1
Institute of Drug Research in Medicine Capital of China , Benxi 117000, P.R. China.

Abstract

A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.

PMID:
29320186
DOI:
10.1021/acs.joc.7b02587

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