title: The asymmetric hetero-Diels-Alder reaction in the syntheses of biologically relevant compounds.
abstract: The hetero-Diels-Alder reaction is one of the most powerful transformations in the chemistry toolbox for the synthesis of aza- and oxa-heterocycles embodying multiple stereogenic centers. However, as compared to other cycloadditions, in particular the dipolar cycloadditions and the Diels-Alder reaction, the hetero-Diels-Alder reaction has been much less explored and exploited in organic synthesis. Nevertheless, this powerful transformation has opened up efficient and creative routes to biologically relevant small molecules and different natural products which contain six-membered oxygen or nitrogen ring systems. Recent developments in this field, in particular in the establishment of enantioselectively catalyzed hetero-Diels-Alder cycloadditions steered by a plethora of different catalysts and the application of the resulting small molecules in chemical biology and medicinal chemistry research, are highlighted in this Minireview.
authors.affiliation: Max-Planck-Institut für molekulare Physiologie, Dortmund (Germany); Technische Universität, Dortmund, Dortmund (Germany).
authors.forename: Vincent
authors.initials: V
authors.lastname: Eschenbrenner-Lux
authors.forename: Kamal
authors.initials: K
authors.lastname: Kumar
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction / Q000379:methods*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings
keywords: asymmetric synthesis; chemical biology; cycloaddition; heterocycles; natural products