Studies on a catalytic version of the Matteson asymmetric homologation reaction

Smith, Keith, Saleh, Basil A., Alshammari, Mohammed B., El-Hiti, Gamal A. and Elliott, Mark ORCID: https://orcid.org/0000-0003-0132-0818 2021. Studies on a catalytic version of the Matteson asymmetric homologation reaction. Organic and Biomolecular Chemistry (19) , pp. 4279-4284. 10.1039/d1ob00604e

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Abstract

Studies of a catalytic asymmetric version of the Matteson reaction between dichloromethylboronates and organolithium reagents have been undertaken. From several different chiral catalytic systems studied, only one based on a mannitol derivative has given substantial asymmetric induction close to that previously achieved with a bis(oxazoline) derivative and ytterbium triflate. More detailed study of the latter reaction revealed that fresh ytterbium triflate actually reduced the level of asymmetric induction, while “aged” ytterbium triflate, or a fresh sample that had been treated with water, brought about improved induction. The implications of these findings are discussed.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Date of First Compliant Deposit:	22 April 2021
Date of Acceptance:	20 April 2021
Last Modified:	05 May 2023 09:23
URI:	https://orca.cardiff.ac.uk/id/eprint/140649

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