Inverse electron-demand Diels–Alder reaction
The Inverse electron demand Diels–Alder reaction, or DAINV or IEDDA 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 DAINV is a cycloaddition between an electron-rich dienophile and an electron-poor diene. During a DAINV reaction, three pi-bonds are broken, and two sigma bonds and one new pi-bond are formed. A prototypical DAINV reaction is shown on the right.
DAINV reactions often involve heteroatoms, and can be used to form heterocyclic compounds. This makes the DAINV reaction particularly useful in natural product syntheses, where the target compounds often contain heterocycles. Recently, the DAINV reaction has been used to synthesize a drug transport system which targets prostate cancer.
The Diels–Alder reaction was first reported in 1928 by Otto Diels and Kurt Alder; they were awarded the Nobel Prize in chemistry for their work in 1950. Since that time, use of the Diels–Alder reaction has become widespread. Conversely, DAINV does not have a clear date of inception, and lacks the comparative notoriety of the standard Diels-Alder. DAINV does not have a clear date of discovery, because of the difficulty that chemists had in differentiating normal from inverse electron-demand Diels-Alder reactions before the advent of modern computational methods. Much of the work in this area is attributed to Dale Boger, though other authors have published numerous papers on the subject.
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