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Catalytic Asymmetric Claisen Rearrangement of Unactivated Allyl Vinyl Ethers.

06:00 EDT 7th August 2010 | BioPortfolio

Summary of "Catalytic Asymmetric Claisen Rearrangement of Unactivated Allyl Vinyl Ethers."

Nearly a century after their original discovery, catalyzed enantioselective variants of the venerable Claisen rearrangement remain relatively rare. We have discovered a cooperative transition metal-Lewis acid cocatalyst system that affects highly enantio- and diastereoselective examples of archetypical Claisen rearrangements. The catalyzed rearrangements proceed using an easily prepared enantioenriched transition metal catalyst and a commercially available Lewis acid cocatalyst at ambient temperature in common solvents.

Affiliation

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260.

Journal Details

This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126
Pages:

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Medical and Biotech [MESH] Definitions

Ethers that are linked to a benzene ring structure.

Compounds containing the vinyl (-C=CH2) functional group.

RNA that has catalytic activity. The catalytic RNA sequence folds to form a complex surface that can function as an enzyme in reactions with itself and other molecules. It may function even in the absence of protein. There are numerous examples of RNA species that are acted upon by catalytic RNA, however the scope of this enzyme class is not limited to a particular type of substrate.

Alkenes with the general formula H2C=CH-CH2-R.

Ordered rearrangement of T-cell variable gene regions coding for the antigen receptors.

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