Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides

Midura, Wanda H.; Ścianowski, Jacek; Banach, Anna; Zając, A.

doi:10.1016/j.tetasy.2014.10.002

Cited by 11 publications

(4 citation statements)

References 24 publications

(2 reference statements)

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“…For example, deprotonation of salts 135 produced ylides 136 , which then reacted with vinyl phosphonates 137 to afford the corresponding cyclopropanes 138 . The products were obtained as mixtures of cis/trans isomers, with each product formed enantioselectively [99b] . A catalytic cyclopropanation employing the ylide obtained from Se ‐benzylation and deprotonation of chiral cyclic selenides 139 a and 139 b was subsequently reported by Chein et al [100] .…”

Section: Chiral Selenium Ylides In the Formation Of Small Ringsmentioning

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: Chiral Selenium Ylides In the Formation Of Small Ringsmentioning

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 ylide 46 obtained from the appropriate selenonium bromide reacted with benzalacetophenone, giving cis-phenyl-dibenzoil-cyclopropane 70a as the main product (Scheme 21). The first application of the optically active selenonium ylides in asymmetric cyclopropanation was reported by Huang's group [62]. At first, they conducted the reactions of exo-and endo-camphor selenonium ylides 75a,b and 76 with various α,β-unsaturated carbonyl compound 77a-l (Scheme 23).…”

Section: Cyclopropanation Reactionsmentioning

confidence: 99%

“…Analysis of the enantiomers showed that their ratio depends on the chiral substituent bonded to the selenonium salts used in the reaction. In 2014, Midura and coworkers reported the asymmetric cyclopropanation of vinyl phosphonates using optically active selenonium ylides derived from (−)-menthol and (+)-limonene [62]. The asymmetric cyclopropanation of vinyl phosphonates 82 and 83 with benzyl terpenyl selenonium salts 84-86 occurred in moderate to good yields (20-54%), while the diastereoselectivity was observed only in the case of vinyl phosphonate 83.…”

Section: Cyclopropanation Reactionsmentioning

confidence: 99%

Selenonium Ylides: Syntheses, Structural Aspects, and Synthetic Applications

2020

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“…However, studies of the synthesis and stereochemistry of organoselenium compounds are somewhat limited. For example, while syntheses of optically active selenonium ylides were reported decades ago, their applications have remained an arcane field of investigation . In 2001, Metzner and co-workers reported the first use of chiral selenonium ylides in asymmetric epoxidation chemistry, as well as a catalytic version thereof .…”

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confidence: 99%

Organoselenium-Catalyzed Asymmetric Cyclopropanations of (E)-Chalcones

2021

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We report a new class of chiral tetrahydroselenophene based on (S)-diphenyl(tetrahydroselenophen-2-yl)methanol, which was prepared from (R)-3-(3-bromopropyl)-2,2-diphenyloxirane and sodium selenide. These chiral tetrahydroselenophene-based compounds were used to catalyze asymmetric cyclopropanation reactions; the selenonium ylide intermediates formed from these selenium-containing catalysts and benzyl bromide efficiently react with (E)-chalcones to give various cyclopropanes (27 examples) with excellent enantioselectivities of ≤99% ee and are the first examples of organoselenium-catalyzed asymmetric cyclopropanations.

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Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides

Cited by 11 publications

References 24 publications

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

Selenonium Ylides: Syntheses, Structural Aspects, and Synthetic Applications

Organoselenium-Catalyzed Asymmetric Cyclopropanations of (E)-Chalcones

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