Asymmetric Baeyer–Villiger Oxidation of 2,3‐ and 2,3,4‐Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H<sub>2</sub>O<sub>2</sub> as the Oxidant

Xu, Senmiao; Wang, Zheng; Zhang, Xumu; Ding, Kuiling

doi:10.1002/ejoc.201001130

Cited by 50 publications

(23 citation statements)

References 59 publications

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“… 272 Mechanistic studies suggested that chiral phosphoric acid plays the role of a bifunctional catalyst to activate both the reactants and the Criegee intermediate in a synergistic manner. 273 , 274 …”

Section: Assembly Of the Lactone Core Structurementioning

confidence: 99%

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

2017

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γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials.

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Section: Assembly Of the Lactone Core Structurementioning

confidence: 99%

Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

2017

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“…On the basis of their success on chiral phosphoric acid‐catalyzed desymmetric B‐V oxidation of 3‐substituted cyclobutanones (see Scheme ), Ding and co‐workers further explored the potential of chiral phosphoric acid catalysts in the B‐V oxidation of racemic 2,3‐disubstituted bicyclic cyclobutanones 30 using 30% aqueous H 2 O 2 as the oxidant . As is illustrated in Scheme , the enantioselective B‐V oxidation gave a range of chiral lactones in moderate to high NL/AL ratios with the NL products as the major regioisomers, when 10 mol% of chiral phosphoric acid 33 was used.…”

Section: Kinetic Resolutionmentioning

confidence: 99%

“…In addition, excellent reactivity was also observed in the oxidation of a 3,3‐disubstituted cyclobutanone, albeit only a moderate ee value was obtained for 42t . The authors also explored the potential of CPA in the desymmetric B‐V oxidation of a tricyclic cyclobutanone ( 43 ) and found that up to 95% ee and almost quantitative yield could be obtained when ( R )‐TRIP was used . Based on these results, they further investigated the charge‐transfer effect on this chiral phosphoric acid‐catalyzed asymmetric B‐V oxidation …”

Section: Desymmetrizationmentioning

confidence: 99%

Advances in Chemocatalytic Asymmetric Baeyer–Villiger Oxidations

et al. 2020

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Baeyer–Villiger oxidations, first reported by Adolf von Baeyer and Victor Villiger 120 years ago, are highly efficient methodologies for the syntheses of esters or lactones from ketones. The asymmetric Baeyer–Villiger oxidations using racemic, prochiral and meso‐cyclic ketones allow a rapid access to chiral lactones, which are valuable intermediates for the subsequent synthesis of bioactive compounds and natural products. The current review provides a summary on the advances in chemocatalytic enantioselective B‐V oxidations. The latest achievements in this field and their applications are presented.

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“…Ding et al. recently extended their study to the BV oxidation of racemic bicyclic ketones, which exemplifies a process of divergent kinetic resolution 68. According to different migratory attitude of the ketonic alkyl moieties and asymmetric induction provided by the organocatalyst, two optically enriched lactones were formed in excellent yield and moderate regioisomeric ratio (Scheme ).…”

Section: Baeyer–villiger Reactionmentioning

confidence: 99%