School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.
Org Biomol Chem. 2012 Sep 14;10(34):6876-84. doi: 10.1039/c2ob26068a. Epub 2012 Jul 31.
A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.
已描述了由手性方酰胺有机催化剂催化的硫代乙酸与α，β-取代硝基烯烃的高对映选择性和非对映选择性的磺酰迈克尔加成。在极低的催化剂负载量（0.2 mol％）下进行的这种有机催化反应以优异的收率，良好的非对映选择性和高对映选择性（高达 94 ： 6 dr，95％ee）提供了合成有用的β-硝基硫醚。此外，还可以在 10 克规模上进行催化反应，并且还呈现了易于转化为牛磺酸衍生物的性质。
