Enantioselective Catalytic Carbonyl–Ene Cyclization Reactions

Grachan, Melissa L.; Tudge, Matthew T.; Jacobsen, Eric N.

doi:10.1002/ange.200704439

Cited by 18 publications

(5 citation statements)

References 35 publications

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“…Under dilute conditions (0.049 mM, 0.045 mol% L 4 -2), catalysis proceeded with up to 840 turnovers over two weeks, which is among the highest reported for intramolecular Prins or carbonyl-ene cyclizations. 60,[75][76][77][78][79]…”

Section: Product Displacement and Turnover (K 3 )mentioning

confidence: 99%

The effect of host structure on the selectivity and mechanism of supramolecular catalysis of Prins cyclizations

et al. 2015

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Section: Product Displacement and Turnover (K 3 )mentioning

confidence: 99%

The effect of host structure on the selectivity and mechanism of supramolecular catalysis of Prins cyclizations

et al. 2015

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“…Various heterocyclic compounds have been synthesized using the oxonium-ene cyclization reaction. 27 The contributions of Overman, 27` b c Mikami, 26,28 Loh, 29 Jacobsen, 30 List, 31 and Trost 32 in this field are noteworthy.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Heterocyclic Scaffolds via Prins, Oxonium-Ene and Related Cyclization Reactions

Saikia¹

2022

Synlett

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A variety of oxygen, nitrogen and sulfur heterocyclic compounds are synthesized via one-pot multicomponent, Prins–, aza–Prins–, thia–Prins–, oxonium–ene–, iminium–ene–, and thionium–ene–cyclization reactions. The reactions proceeds with high diastereo– and region–selectivity. Importantly, C–C, C–N, C–O and C–S bonds are formed in a single step. These procedures are extended for the synthesis of biologically active molecules and natural products.

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“…Scheme4.Completion of the analogue syntheses. ed [21] the efficacy of related catalysts in promoting intramolecular ene reactions.W ed ecided to reexamine this reaction with C39 derivatized as ap rimary acetate to determinew hether the electron-donating C39 methyl group promoted the undesired decomposition in the prior studies. The reviseds equence is shown in Scheme 5.…”

mentioning

confidence: 99%

Potent and Readily Accessible Bistramide A Analogues through Diverted Total Synthesis

Hanna

Naro

Deiters

et al. 2018

Chemistry A European J

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A diverted total synthesis effort is described that is designed to prepare potent cytotoxins based on the actin-binding natural product bistramide A. The major focus of this study is the preparation of analogues that contain oxygenation at the C29 position, which is necessary for a key reaction in the sequence but is not present in the natural product. This process showed that C29 ketone analogues are accessed more readily and show similar potency compared to the natural product. The ability to incorporate C29 oxygenation and to replace a secondary alcohol by a primary alcohol allowed for the development of a more convergent approach that provides a potent analogue in just eight steps in its longest linear sequence.

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Enantioselective Catalytic Carbonyl–Ene Cyclization Reactions

Cited by 18 publications

References 35 publications

The effect of host structure on the selectivity and mechanism of supramolecular catalysis of Prins cyclizations

The effect of host structure on the selectivity and mechanism of supramolecular catalysis of Prins cyclizations

Synthesis of Heterocyclic Scaffolds via Prins, Oxonium-Ene and Related Cyclization Reactions

Potent and Readily Accessible Bistramide A Analogues through Diverted Total Synthesis

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