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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 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: 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: 11 Jun 2021 12:28
URI: https://orca.cardiff.ac.uk/id/eprint/140649

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