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Iron-mediated highly diastereoselective allylation of carbonyl compounds with cyclic allylic halides

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Abstract

An efficient iron-mediated highly diastereoselective allylation of carbonyl compounds with cyclic allylic halides is reported. The allylation reactions involving various carbonyl compounds proceeded efficiently in the presence of 20 mol% bismuth(III) chloride to give the corresponding homoallylic alcohols in moderate to good yields with excellent diastereoselectivities and wide functional group tolerance. In cases where an aldehyde and a ketone (e.g., 2-pyridinecarboxaldehyde and phenylglyoxylic acid) containing an adjacent chelating atom were used, complete reversal of product diastereoselectivities was observed which could be explained by the Cram-chelated six-membered ring transition state.

Graphical abstract: Iron-mediated highly diastereoselective allylation of carbonyl compounds with cyclic allylic halides

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Publication details

The article was received on 06 Feb 2019, accepted on 25 Mar 2019 and first published on 26 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00210C
Citation: Org. Chem. Front., 2019, Advance Article

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    Iron-mediated highly diastereoselective allylation of carbonyl compounds with cyclic allylic halides

    X. Liu, B. Cheng, Y. Guo, X. Chu, W. Rao, T. Loh and Z. Shen, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00210C

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