Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro-nucleophiles to <i>N</i>
-<i>tert</i>
-Butanesulfinyl Imines
作者:Manas Das、Donal F. O'Shea
DOI:10.1002/chem.201503354
日期:2015.12.14
Addition of organotrimethylsilane reagents to chiral N‐tert‐butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO−/Bu4N+ as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N‐tert‐butanesulfinyl amides. Remarkably
organotrimethylsilane试剂的手性的加成ñ -叔-butanesulfinyl亚胺可以在良好的产率和具有优良的非对映选择性通过采用TMSO来实现- /卜4 Ñ +作为在THF中的路易斯碱的活化剂。多种脂族,芳族,杂芳族和有机金属的手性亚胺的被用作亲电子对的对映体富集的合成Ñ -叔-butanesulfinyl酰胺。值得注意的是,同一组反应条件可用于范围广泛的台式稳定有机三甲基硅烷试剂,这凸显了该方法的通用性和稳健性。