Pandidurai Solai, Kumar Choutipalli Venkata Surya, Subramanian Venkatesan, Sekar Govindasamy
Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamil Nadu, India.
Centre for High Computing, CSIR-Central Leather Research Institute, Chennai, 600020, Tamil Nadu, India.
Org Lett. 2024 Apr 19;26(15):2971-2975. doi: 10.1021/acs.orglett.4c00544. Epub 2024 Mar 28.
An efficient approach for the synthesis of chiral pyrrolo[1,2-][1,4]thiazine-2-carbaldehydes is achieved via formal 1,3-dipolar cycloaddition/rearrangement reactions of benzothiazolium salt and α,β-unsaturated aldehydes, utilizing an asymmetric organocatalyst. This process results in the formation of fluorescent, highly enantioenriched chiral molecules with three contiguous stereogenic centers, one of which is a chiral quaternary center, with excellent yields and enantio- and diastereoselectivity. A computational study demonstrated the understanding of the reaction mechanism. The synthetic utility of this protocol was successfully employed for gram scale synthesis. Fluorescent and in silico studies showed the application of the present methodology.
通过苯并噻唑鎓盐与α,β-不饱和醛的形式上的1,3-偶极环加成/重排反应，利用不对称有机催化剂，实现了一种高效合成手性吡咯并[1,2 - ][1,4]噻嗪-2-甲醛的方法。该过程形成了具有三个连续立体中心的荧光、高度对映体富集的手性分子，其中一个是手性季碳中心，产率、对映选择性和非对映选择性均优异。一项计算研究表明了对反应机理的理解。该方案的合成效用成功用于克级规模的合成。荧光和计算机模拟研究展示了本方法的应用。
