Synthesis of azimic acid using hydroformylation

Bates, Roderick W.; Kasinathan, Sivarajan

doi:10.1016/j.tet.2013.01.060

Cited by 13 publications

(8 citation statements)

References 37 publications

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“…A related transformation was employed in the total synthesis of azimic acid (120) that was reported by Bates and Kasinathan in 2013. 55 The synthetic challenge for this compound is the all-cis configuration of three stereocenters on the piperidine ring. The researchers group used double hydroformylation, followed by intramolecular enamine formation with one of the introduced aldehyde groups in a tandem pathway, leading to the ring closure.…”

Section: Review Syn Thesismentioning

confidence: 99%

Carbonylations of Alkenes in the Total Synthesis of Natural Compounds

Gehrtz¹,

Hirschbeck²,

Ciszek³

et al. 2016

Synthesis

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The goal of this review is to highlight the applications of carbonylation reactions of alkenes in the total synthesis of natural compounds. These highly atom-economic reactions, which are known for their industrial applications, constitute attractive synthetic methodologies for the selective construction of carbonyl compounds. We aimed at the selection of recent methodologically attractive syntheses where carbonylations were applied as key steps. In addition, a few examples of the related carbonylation of allenes are shown.

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Section: Review Syn Thesismentioning

confidence: 99%

Carbonylations of Alkenes in the Total Synthesis of Natural Compounds

Gehrtz¹,

Hirschbeck²,

Ciszek³

et al. 2016

Synthesis

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“…Cyclic enamines bearing an electron‐withdrawing protecting group on nitrogen, such as ene‐sulfonamide 1 a , have been shown to be useful precursors to oxygenated piperidines by hydroboration–oxidation, epoxidation‐ring opening and by dihydroxylation . This chemistry has been used in this laboratory for the stereoselective synthesis of pseudoconhydrine, azimic acid, and 5‐hydroxysedamine . We were attracted to the idea of using these ene‐sulfonamides for carbon–carbon bond formation.…”

Section: Introductionmentioning

confidence: 99%

Platinum‐Catalysed Ring‐Opening Isomerisation of Piperidine Cyclopropanes

2018

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Ar ange of cyclopropyl-fused N-tosyl piperidines have been synthesised ands hown to undergo ring-opening isomerisation on treatment with platinum(II) catalysts. The products can have either an endo-cyclic or exo-cyclic double bond. The selectivity is influenced by reaction temperature, solventa nd, most significantly,t he catalyst. Am echanism in-volvingC ÀCb ond activation and b-hydride eliminationi s proposed. When b-hydride elimination is blocked, as tereospecific platinum-driven Wagner-Meerwein shift is observed.

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“…The thermal cyclodehydration of α-amido ester 8 afforded 1n in 71% yield. Next, the decarboxylative HDA reaction conducted to the formal synthesis of (±)-azimic acid in a total of three steps and 32% overall yield (previously shortest reported formal synthesis: five steps; 9% yield). , Furthermore, to the best of our knowledge, this approach would also constitute the shortest currently reported synthesis described in the literature. As a further example, the total synthesis of (±)-deoxocassine was also undertaken.…”

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confidence: 97%