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Asymmetric Diels-Alder reaction is one step in the biosynthesis of the statin lovastatin. [60] The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6.
Otto Paul Hermann Diels (German pronunciation: [ˈɔto ˈdiːls] ⓘ; 23 January 1876 – 7 March 1954) was a German chemist. His most notable work was done with Kurt Alder on the Diels–Alder reaction, a method for cyclohexene synthesis. [1] The pair was awarded the Nobel Prize in Chemistry in 1950 for their work.
The inverse electron demand Diels–Alder reaction, or DA INV or IEDDA [1] is an organic chemical reaction, in which two new chemical bonds and a six-membered ring are formed. It is related to the Diels–Alder reaction , but unlike the Diels–Alder (or DA) reaction, the DA INV is a cycloaddition between an electron-rich dienophile and an ...
The aza Diels-Alder reaction may occur either by a concerted or stepwise process. The lowest-energy transition state for the concerted process places the imine lone pair (or coordinated Lewis acid) in an exo position. Thus, (E) imines, in which the lone pair and larger imine carbon substituent are cis, tend to give exo products. [2]
Like the Diels–Alder reaction, the rDA preserves configuration in the diene and dienophile. Much less is known about the relative rates of reversion of endo and exo adducts, and studies have pointed to no correlation between relative configuration in the cyclohexene starting material and reversion rate.
The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines named after its inventor Dale L. Boger, who first reported it in 1981. [1] The reaction is a form of inverse-electron demand Diels-Alder reaction in which an enamine reacts with a 1,2,4-triazine to form the pyridine nucleus.
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In organic chemistry, an intramolecular Diels-Alder cycloaddition is a Diels–Alder reaction in which the diene and the dienophile are both part of the same molecule. [1] The reaction leads to the formation of the cyclohexene-like structure as usual for a Diels–Alder reaction, but as part of a more complex fused or bridged cyclic ring system.