Deuterium as a stereochemically invisible blocking group for chiral ligand synthesis

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

Preview

PDF (Accepted manuscript) - Accepted Version Download (295kB) | Preview

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
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
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

Downloads

Actions (login required)

View Item