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Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification

Georgiou, I; Whiting, A

Authors

I Georgiou



Abstract

The use of homoboroproline as a bifunctional catalyst in the asymmetric aldol reaction has been investigated mechanistically, particularly with respect to tuning the Lewis acidity of boron by in situ esterification with mildly sigma-electron withdrawing diols such as hydrobenzoin and tartrate esters. The stability of simple cyclohexyl and cyclopentyl boronate diol esters shows that the 5-ring boronate esters are more stable, which sheds light on the mode of action of esterified homoboroproline catalyst in the enamine-mediated aldol reaction, which is also studied by NMR. The result is reaction optimisation to provide an efficient aldol reaction and a proposed mechanistic proposal.

Citation

Georgiou, I., & Whiting, A. (2012). Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification. Organic and Biomolecular Chemistry, 10(12), 2422-2430. https://doi.org/10.1039/c2ob06872a

Journal Article Type Article
Publication Date 2012-03
Deposit Date May 2, 2013
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 10
Issue 12
Pages 2422-2430
DOI https://doi.org/10.1039/c2ob06872a
Public URL https://durham-repository.worktribe.com/output/1457680