College of Chemistry and Molecular Sciences, Wuhan University, 430072, China.
Org Lett. 2011 Aug 19;13(16):4426-9. doi: 10.1021/ol201766k. Epub 2011 Jul 26.
The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-γ-trifluoromethyl γ-sulfone hydroxamate.
首次实现了手性中心带有独特的三氟甲基和硫原子的 4,4,4-三氟巴豆酸酯与硫醇的不对称磺酰迈克尔加成，使用 1 mol%双功能有机催化剂，以高产率和优异的对映选择性得到产物。随后的转化导致了对映体富集的硫代色满-4-酮和强效 MMP-3 抑制剂的关键中间体 (R)-γ-三氟甲基 γ-砜羟胺的简便制备。
