Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates.
basic_science · Level V
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- Record sourced from PubMed, PMID 15060277.
- Also identified by PMC identifier 397391.
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Abstract
Chiral dirhodium(II) carboxamidates are highly efficient catalysts for reactions between a variety of aldehydes and activated dienes. Catalyst loadings as low at 0.01 mol % have been realized with enantioselectivities up to 97%. Kinetic investigations reveal a pronounced electronic influence on the rate of the hetero-Diels-Alder reaction with a Hammett rho value of +1.9 (versus sigma(+)). Inhibition of the catalyst by reactant aldehyde is apparent, but reactions show first-order dependence on aldehyde and diene, and there is a variable dependence on catalyst.
Medical subject headings
- Aldehydes
- Alkenes
- Organometallic Compounds
- Rhodium