PROF.DR . NAZ M ATABAY

DEPARTMENT OF CHEMISTRY

FATIH UNIVERSITY

MSc.student . NABEEL B AZEEZ

INTRODUCTIONTHE REACTION REACTION MECHANISMSTEREOSELECTIVITYRETROSYNTHETIC ANALYSIS

RECENT LITERATURE

REFRENCES

Diels-Alder Reaction

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Otto Diels Kurt Alder

• .diene synthesis has developed into one of the most important working methods in organic chemistry .

• The method has also proved valuable in a great many ways in research into the constitution of complex natural products .

• formed by diene synthesis are usually

stable.

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The Diels–Alder reaction is particularly useful in synthetic organic

chemistry as a reliable method for forming 6-membered systems with good

control over regio- and stereo chemical properties. The underlying concept

has also been applied to other π-systems, such as carbonyls and imines, to

furnish the corresponding heterocyclic, known as the hetero-Diels–Alder

reaction. Diels–Alder reactions can be reversible under certain conditions;

the reverse reaction is known as the retro-Diels–Alder reaction.

conjugated diene dienophile cyclohexene

between a conjugated diene and a substituted alkene, commonly

termed the dienophile, to form a substituted cyclohexene system

A conjugated diene reacts with a double-bonded dienophile

Normally, dienes are electron-rich; dienophiles are electron-poor

Normally, dienes are electron-rich; dienophiles are electron-poor

Diels–Alder reactions, as concerted cycloadditions, are tereospecific, i.e. stereo chemical information in the reactants is retained in the products. E- and Z-dienophiles, for example, give rise to the adducts with corresponding syn or anti-stereochemistry

Retro synthetic analysis using theDiels-Alder reaction

* Organic chemistry; Clayden, J.; Greeves, N.; Warren, S.;

Wothers, P. Oxford University Press, Oxford, 2006.

* Lewis Acids and Selectivity in Organic Synthesis; Santelli, M.;

Pons, J. CRS Press, USA, 1995.\* http://www.organic-

chemistry.org/namedreactions/diels-alder-reaction.shtm

* Wikipedia.co.uk