6581-69-7Relevant academic research and scientific papers
Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes
Sachse, Florian,Gebauer, Konrad,Schneider, Christoph
, p. 64 - 71 (2020/11/30)
Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.
Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers
Wang, Shengzheng,Zhang, Yongqiang,Dong, Guoqiang,Wu, Shanchao,Zhu, Shiping,Miao, Zhenyuan,Yao, Jianzhong,Li, Hao,Li, Jian,Zhang, Wannian,Sheng, Chunquan,Wang, Wei
supporting information, p. 5570 - 5573 (2013/11/19)
An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.
Thioaldehyde Diels-Alder Reactions
Vedejs, E.,Eberlein, T. H.,Mazur, D. J.,McClure, C. K.,Perry, D. A.,et al.
, p. 1556 - 1562 (2007/10/02)
Thioaldehydes containing virtually any α-substitutent can be generated by photofragmentation of phenacyl sulfides.Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advan
