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Arthurs, Ross A. and Richards, Christopher J. 
ORCID: https://orcid.org/0000-0001-7899-4082
(2017)
Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis.
Organic Letters, 19 (3).
pp. 702-705.
ISSN 1523-7060
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Abstract
Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science Faculty of Science > School of Chemistry |
| Depositing User: | Pure Connector |
| Date Deposited: | 30 Mar 2017 00:42 |
| Last Modified: | 22 Oct 2022 02:29 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/63118 |
| DOI: | 10.1021/acs.orglett.6b03874 |
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