A temperature study on a stereoselective organocatalyzed aldol reaction in water

作者：Emer Enrico; Galletti Paola; Giacomini Daria^*

来源：Tetrahedron, 2008, 64(49): 11205-11208.

DOI：10.1016/j.tet.2008.09.059

We report the first temperature Study on the stereoselectivity of the 'in-water' aldol reaction between nicotinaldehyde (3-pyridinecarbaldehyde) and cyclohexanone catalyzed by morpholine and trans-4-tert-butyldimethylsilyloxy-L-proline. Eyring plots of diastereomeric ratio anti/syn gave a constant diastereoselectivity with respect to reaction temperature using morpholine as catalyst. With O(TBS)-L-proline we observed a non-linear behaviour of the Eyring plot with the presence of an inversion temperature (T(inv)), which disclosed dynamic solvation effects in water.

• 出版日期2008-12-1