The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile

Hulme, Christopher; Morrissette, Matthew M.; Volz, F. A.; Burns, Christopher J.

doi:10.1016/s0040-4039(97)10795-x

Cited by 104 publications

(41 citation statements)

References 20 publications

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“…In the case of a-amino acid derivatives as acid partners, the dipeptide 67 was obtained with almost no diastereoselectivity, regardless of the aldehyde, the isocyanide, or the side chain of the acid (Scheme 28). [108] Similar results were obtained when a solution of ammonia was used instead of the amine, [109] or when the isocyanide was bound to a solid phase. [110] Even the use of polyfunctionalized b-amino acid derivatives did not lead to any diastereoselectivity.…”

Section: Four-component Approachsupporting

confidence: 58%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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Section: Four-component Approachsupporting

confidence: 58%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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“…A side product is the noncyclized amine. [209,210] Szardenings et al from the company Affymax have described another route to dioxopiperazines by means of U-4CR (Scheme 14). [211] An a-amino acid anchored to the resin with its carboxyl group as the amine component, a Boc-protected a-amino acid, an oxo component, and an isocyanide react in a U-4CR and can then be cyclized to dioxopiperazines such as 247 under acidic conditions.…”

Section: Multicomponent Reactions With Isocyanidesmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,969

1,635

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Multicomponent reactions (MCRs) are fundamentally different from two‐component reactions in several aspects. Among the MCRs, those with isocyanides have developed into popular organic‐chemical reactions in the pharmaceutical industry for the preparation of compound libraries of low‐molecular druglike compounds. With a small set of starting materials, very large libraries can be built up within a short time, which can then be used for research on medicinal substances. Due to the intensive research of the last few years, many new backbone types have become accessible. MCRs are also increasingly being employed in the total synthesis of natural products. MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures. However, this requires that the chemist learns the “language” of MCRs, something that this review wishes to stimulate.

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“…Ein Nebenprodukt ist das nichtcyclisierte Amin. [209,210] Szardenings et al von der Firma Affymax haben einen anderen Weg zu Dioxopiperazinen durch U-4CR beschrieben (Schema 14). [211] Eine über die Carbonsäuregruppe am Harz verankerte a-Aminosäure als Aminkomponente, eine Bocgeschützte a-Aminosäure, eine Oxokomponente und ein Isocyanid reagieren in einer U-4CR und können anschlieûend unter sauren Bedingungen zu Dioxopiperazinen wie 247 cyclisiert werden.…”

Section: Mit Bifunktionellen Ausgangsverbindungen Zu Cyclischen Variaunclassified

Multikomponentenreaktionen mit Isocyaniden

2000

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EinleitungOrganisch-chemische Synthesen haben einen hohen Grad an Kunstfertigkeit erlangt. Kaum ein komplizierter Naturstoff entzieht sich einer vielstufigen Totalsynthese. Dabei werden die Zielmoleküle oft mehr divergent als konvergent, also sequentiell, entsprechend ihrer Komplexität in vielen Schritten synthetisiert. Der Fortschritt in der Totalsynthese von Naturstoffen der vergangenen Jahrzehnte lässt sich beim Vergleich der Strychninsynthese von Woodward mit neueren Synthesen erkennen. [1] Er beruht z. T. auf der Optimierung von Syntheseoperationen und Reaktionen. Metallorganische Varianten klassischer Reaktionen sind häufig diastereo-, enantio-, regio-und/oder chemoselektiver und liefern die Produkte oft in besseren Ausbeuten. Verbesserte analytische sowie Trennmethoden tragen zu effizienteren Syntheseschritten bei. Während Woodward für seine 28-stufige Strychninsynthese 6 Â 10 À5 % Gesamtausbeute erhielt, konnten die Gruppen von Magnus, Overman, Kuehn und Rawal diese komplexe Verbindung in weniger Syntheseschritten und in 10 3 -bis 10 4 -mal höherer Gesamtausbeute herstellen.

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The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile

Cited by 104 publications

References 20 publications

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Multicomponent Reactions with Isocyanides

Multikomponentenreaktionen mit Isocyaniden

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