Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 13, Pages 5200-5207Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4007244
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Funding
- Aarhus University
- Carlsberg Foundation
- FNU
- CONACYT (Mexico)
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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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