Skardon-Duncan, J., Sparenberg, M., Bayle, A., Alexander, S. and Clark, J. S. (2018) Stereoselective synthesis of medium-sized cyclic ethers by sequential ring-closing metathesis and Tsuji–Trost allylation. Organic Letters, 20(9), pp. 2782-2786. (doi: 10.1021/acs.orglett.8b01082) (PMID:29676923)
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Abstract
Fully functionalized medium-sized cyclic ethers, of the type found in fused polyether natural products, have been prepared by sequential ring-closing diene metathesis, conversion of the resulting cyclic enone into an allylic enol carbonate, and Tsuji–Trost allylation using a chiral palladium complex. Very high levels of diastereocontrol, favoring the diastereomer in which there is a cis relationship between the allyl group at C-2 of the medium-ring ether and the substituent at C-7/C-8, are obtained in cases where catalyst control and substrate control are matched.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Clark, Professor Stephen and Skardon-Duncan, James and Alexander, Mr Samuel |
| Authors: | Skardon-Duncan, J., Sparenberg, M., Bayle, A., Alexander, S., and Clark, J. S. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Organic Letters |
| Publisher: | American Chemical Society |
| ISSN: | 1523-7060 |
| ISSN (Online): | 1523-7052 |
| Published Online: | 20 April 2018 |
| Copyright Holders: | Copyright © 2018 American Chemical Society |
| First Published: | First published in Organic Letters 20(9):2782-2786 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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