Issue 10, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Feb 2019
Accepted
25 Mar 2019
First published
26 Mar 2019

Org. Chem. Front., 2019,6, 1581-1586

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, 6, 1581 DOI: 10.1039/C9QO00210C

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