1428246-06-3Relevant articles and documents
Asymmetric organocatalytic thio-diels-alder reactions via trienamine catalysis
Jiang, Hao,Cruz, David Cruz,Li, Yang,Lauridsen, Vibeke Henriette,J?rgensen, Karl Anker
supporting information, p. 5200 - 5207 (2013/05/22)
We report a new process to access highly enantioenriched sulfur-based heterocycles by an asymmetric catalytic thio-Diels-Alder reaction. Thiocarbonyls are challenging heterodienophiles in enantioselective Diels-Alder reactions, due to their inherent high reactivity and their poor ability to coordinate to chiral catalysts. We successfully circumvented these problems by employing a different strategy, which explores the use of in situ generated catalyst-bound dienes. Synthetically useful dihydrothiopyrans as well as other bi- and tricyclic sulfur-containing heterocycles are formed in high yields and high to excellent selectivities. DFT calculations were performed to examine the mechanism of the developed reaction. Furthermore, a series of synthetic transformations of the optically active sulfur-based heterocycles are presented.