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  • Title: Asymmetric organocatalytic thio-Diels-Alder reactions via trienamine catalysis.
    Author: Jiang H, Cruz DC, Li Y, Lauridsen VH, Jørgensen KA.
    Journal: J Am Chem Soc; 2013 Apr 03; 135(13):5200-7. PubMed ID: 23473536.
    Abstract:
    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.
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