Enantioselective cyclization of symmetric diesters

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Jennifer E. Wilent (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/
Kimberly Petersen

Abstract: Two important facets that are found in many biologically active compounds and complex natural products are chirality and heterocyclic motifs, in particular lactones and lactams. Biologically active compounds found in nature often need to be synthesized due to the fact that only a minute amount of the active molecule is produced. In the research described herein, an asymmetric methodology known as desymmetrization is utilized to produce enantioenriched compounds that can be used as building blocks in the synthesis of biologically active natural products. We have developed an efficient synthesis of enantioenriched ?-and d-lactones via an enantioselective desymmetrization. In this process, racemic diesters in the presence of a chiral Brønsted acid selectively undergo cyclization to yield enantioenriched ?- and d-lactones. The methodology is also expanded to include the synthesis of spirocyclic molecules. The desymmetrization is highly selective and the products formed contain an all-carbon quaternary stereocenter that would be difficult to install using other methodologies.

Additional Information

Language: English
Date: 2016
Lactones $x Synthesis
Lactams $x Synthesis
Asymmetric synthesis
Enantioselective catalysis

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