Site‐Selective Synthetic Modifications of the Cinchona Alkaloids

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 7, 2024

Abstract The natural product quinine has been known to humankind for centuries, and in that time played a pivotal role the treatment of malaria. Quinine, related cinchona alkaloids, have seen widespread contemporary use across chemical biological disciplines, owing part plethora functional groups stereochemical information contained within their scaffold. This review focuses on site‐selective synthetic modifications alkaloids. Our comparative analysis may act as ‘user manual’ selective functionalisation aims promote consideration remarkable lesser‐understood aspects chemistry.

Язык: Английский

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Taming Tethered Nitreniums for Alkene Functionalization Reactions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(20), С. 15352 - 15357

Опубликована: Окт. 10, 2024

We present the first examples of amino-trifluoroacetoxylations alkenes using N-alkoxy carbamate tethers. Hypervalent iodine oxidants mediate this transformation, providing a "green" alternative to existing intramolecular amino-hydroxylation protocols which use toxic metals such as osmium. In all cases examined, reaction is regioselective and stereospecific, with geometry starting alkene controlling diastereomeric outcome. By analogy prior art from our own observations, we posit that transient nitrenium species serves key intermediate.

Язык: Английский

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Iron-catalysed intramolecular C(sp³)–H amination of alkyl azides

Chemical Communications, Год журнала: 2024, Номер 60(95), С. 13998 - 14011

Опубликована: Янв. 1, 2024

Iron-catalysed intramolecular C(sp

Язык: Английский

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