One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling,thioester substrates,and reactions in ester solvents |
| |
Authors: | C Wade Downey Grant J Dixon Jared A Ingersoll Claire N Fuller Kenneth W MacCormac Anna Takashima Rohina Sediqui |
| |
Institution: | University of Richmond, Gottwald Center for the Sciences, 28 Westhampton Way, Richmond, VA 23173, United States |
| |
Abstract: | Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed. |
| |
Keywords: | Corresponding author UVRWUYAKBXOLRF-UHFFFAOYSA-N PVPZPTBAOYEVPX-UHFFFAOYSA-N PDNSCUIMVQOXGU-VAWYXSNFSA-N YOBKMVIDKOVCBB-UHFFFAOYSA-N GXIRLMYDCAZKCQ-UHFFFAOYSA-N LXPTZDCZHVGGBU-UHFFFAOYSA-N Enol silane Mukaiyama aldol Silyl triflate Aldehyde-aldehyde coupling |
本文献已被 ScienceDirect 等数据库收录! |