I Georgiou
Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification
Georgiou, I; Whiting, A
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 |
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