Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines
Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines
复制标题
DOI：
10.1021/acs.joc.0c01931
复制
发表时间：
2020-10-16
影响因子：
3.6
通讯作者：
Masson, Geraldine
中科院分区：
文献类型：
--
作者：
Lyu, Jiyuan;Claraz, Aurelie;Masson, Geraldine
基于手性磷酸的有机催化和可见光催化都是精细化学品可持续生产的有前途的技术。在这种情况下，我们设想了一类新的嵌合催化实体的设计和合成，将具有两种催化能力。鉴于其多任务性质，这类催化剂对于开发新的催化转化，特别是串联工艺特别有吸引力。为了实现这一目标，已经制备和研究了几种基于BINOL的手性磷酸主链，其呈现一个或两个可见光敏感的噻吨酮部分。这些新的光活性手性有机催化剂的效用，然后证明在对映选择性串联三组分亲电胺化enecarbamates。值得注意的是，C-1对称的有机/光催化剂已经显示出比呈现C-2对称的那些更好的催化活性。
Chiral phosphoric acid based organocatalysis and visible-light photocatalysis have both emerged as promising technologies for the sustainable production of fine chemicals. In this context, we have envisioned the design and the synthesis of a new class of chimeric catalytic entities that would feature both catalytic capabilities. Given their multitask nature, such catalysts would be particularly attractive for the development of new catalytic transformations, tandem processes in particular. Toward this goal, several BINOL-based chiral phosphoric acid backbones presenting one or two visible-light-sensitive thioxanthone moieties have been prepared and studied. The utility of these new photoactive chiral organocatalysts is then demonstrated in the enantioselective tandem three-component electrophilic amination of enecarbamates. Of note, the C-1-symmetric organo/photocatalyst has shown a better catalytic activity than those presenting a C-2 symmetry.