Synthesis of diastereomeric bis(oxazoline) ligands derived from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene

Arthurs, Ross A. and Richards, Christopher J. (2018) Synthesis of diastereomeric bis(oxazoline) ligands derived from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene. Synlett, 29 (5). pp. 585-588. ISSN 0936-5214

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Abstract

Starting from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene, all possible 2-trimethylsilyl- and 2,2′-di(trimethylsilyl)-substituted diastereoisomers, potential bisoxazoline ligands for use in asymmetric catalysis, were synthesised by selective lithiation followed by addition of trimethylsilyl chloride. Access to the (S,S,R p,R p)-diastereoisomer was achieved following diastereoselective introduction of two deuterium-blocking groups and utilisation of the high k H/k D value for lithiation, methodology that was also applied to the synthesis of a related 2,2′-di(diphenylmethanol)bisoxazoline ligand.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	LivePure Connector
Date Deposited:	05 Feb 2019 13:30
Last Modified:	28 Jun 2025 00:36
URI:	https://ueaeprints.uea.ac.uk/id/eprint/69852
DOI:	10.1055/s-0036-1589163

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