Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification |
| |
Authors: | Georgiou Irene Whiting Andrew |
| |
Institution: | Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, Science Laboratories, South Road, Durham DH1 3LE, UK. |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|