Deuterium as a Stereochemically Invisible Blocking Group for Chiral Ligand Synthesis

Arthurs, Ross A. and Richards, Christopher J. (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: 28 Oct 2019 16:01
URI: https://ueaeprints.uea.ac.uk/id/eprint/63118
DOI: 10.1021/acs.orglett.6b03874

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