Kinetic resolution of 2-methoxycarbonylalk-3-enols through a stereoselective cyclofunctionalization promoted by an enantiomerically pure electrophilic selenium reagent

Tomassini, Cristina; Sarra, Francesca Di; Monti, Bonifacio; Sancineto, Luca; Bagnoli, Luana; Marini, Francesca; Santi, Claudio

doi:10.3998/ark.5550190.p009.826

Cited by 2 publications

(2 citation statements)

References 11 publications

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“…Computations suggested a supramolecular pathway involving extensive hydrogen bonding and coordination between the selenium atoms of NPSP and 31 . Cyclofunctionalizations have also been employed by Santi et al [30] . in kinetic resolutions of unsaturated alcohols, as in the racemic mixtures of 33 , where 33 a underwent selective cyclization, while 33 b was recovered largely intact (Scheme 9).…”

Section: Cyclofunctionalizationsmentioning

confidence: 99%

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Stadel,

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2024

Chemistry A European J

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The discovery and synthetic applications of novel organoselenium compounds and their reactions proceeded rapidly during the past fifty years and such processes are now carried out routinely in many laboratories. At the same time, the growing demand for new enantioselective processes provided new challenges. The convergence of selenium chemistry and asymmetric synthesis led to key developments in the 1970s, although the majority of early work was based on stoichiometric processes. More recently, greater emphasis has been placed on greener catalytic variations, along with the discovery of novel reactions and a deeper understanding of their mechanisms. The present review covers the literature in this field from 2010 to early 2023 and encompasses asymmetric reactions mediated by chiral selenium‐based reagents, auxiliaries and, especially, catalysts. Protocols based on achiral selenium compounds in conjunction with other species of chiral catalysts, as well as reactions that are controlled by chiral substrates, are also included.

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Section: Cyclofunctionalizationsmentioning

confidence: 99%

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Stadel,

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2024

Chemistry A European J

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“…[6] To the best of our knowledge we also reported the first example of non-enzymatic kinetic resolution of allylic alcohols through an electrophilic methoxyselenenylation reaction [7] and, more recently,t he kinetic resolution of 2-cabomethoxy-3-alkenols exploiting a cyclofunctionalization with the formation of functionalized tetrahydrofurans. [8] In both cases half equivalent of electrophilic reagent activates the stereoselective interor intramolecular addition to the double bond leaving unreacted half equivalent of enantiomerically enriched starting material. The yields are generally good and the enantiomeric excess ranges from 70% up to 95% (Scheme 1)…”

Section: Enantiomerically Pure Diselenides In Asymmetric Synthesismentioning

confidence: 99%

Organic Diselenides: Versatile Reagents, Precursors, and Intriguing Biologically Active Compounds

Santi¹,

Tomassini

Sancineto

2017

Chimia

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In this account, we describe how some organic diselenides were successfully used in the past as reagents for asymmetric stereoselective synthesis and more recently as precursors of catalysts and reagents applied in new green protocols. A biomimetic approach offered the possibility to perform oxidative reactions using hydrogen peroxide as oxidant and water as medium affording the desired products in excellent yields under mild conditions. The umpolung of the selenium atom gave novel nucleophilic reagents having a strongly accelerated reaction rate in on water conditions. Finally, the use of diselenides to exploit specific biological activities is described here as seminal examples of a promising field of research currently under investigation in our group.

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Kinetic resolution of 2-methoxycarbonylalk-3-enols through a stereoselective cyclofunctionalization promoted by an enantiomerically pure electrophilic selenium reagent

Cited by 2 publications

References 11 publications

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Organic Diselenides: Versatile Reagents, Precursors, and Intriguing Biologically Active Compounds

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