Asymmetric Cyclopropanation of Olefins Catalyzed by a Chiral Cobalt(II) Porphyrin

Berkessel, Albrecht; Ertuerk, Erkan; Neudoerfl, Joerg M.

doi:10.25135/acg.oc.11.17.04.019

Cited by 4 publications

(1 citation statement)

References 12 publications

(23 reference statements)

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“…Up to 80:20 trans:cis diastereoisomeric ratio and 82% ee were achieved with 96% total yield within 1 h at ambient temperature, by using this Co(II) chiral porphyrin complex as catalyst. On the other hand, the cyclopropanation of 1,1-diphenylethylene with EDA catalysed by the same Co(II) porphyrin gave the corresponding cyclopropane in moderate yield (62%) and 50% ee [ 55 ].…”

Section: Cyclopropanation Reactionsmentioning

confidence: 99%

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group

et al. 2018

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Carbene transfer reactions are very important transformations in organic synthesis, allowing the generation of structurally challenging products by catalysed cyclopropanation, cyclopropenation, carbene C-H, N-H, O-H, S-H, and Si-H insertion, and olefination of carbonyl compounds. In particular, chiral and achiral metalloporphyrins have been successfully explored as biomimetic catalysts for these carbene transfer reactions under both homogeneous and heterogeneous conditions. In this work the use of synthetic metalloporphyrins (MPorph, M = Fe, Ru, Os, Co, Rh, Ir, Sn) as homogeneous or heterogeneous catalysts for carbene transfer reactions in the last years is reviewed, almost exclusively focused on the literature since the year 2010, except when reference to older publications was deemed to be crucial.

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Section: Cyclopropanation Reactionsmentioning

confidence: 99%

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group

et al. 2018

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Picket-fence ruthenium(II) phthalocyaninates bearing (1R,2S,5R)-menthoxy groups as prototype of chiral catalysts

Kroitor,

Sinelshchikova,

Grigoriev

et al. 2024

Dyes and Pigments

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Carbene Radicals in Transition-Metal-Catalyzed Reactions

et al. 2023

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Discovered as organometallic curiosities in the 1970s, carbene radicals have become a staple in modern-day homogeneous catalysis. Carbene radicals exhibit nucleophilic radical-type reactivity orthogonal to classical electrophilic diamagnetic Fischer carbenes. Their successful catalytic application has led to the synthesis of a myriad of carbo- and heterocycles, ranging from simple cyclopropanes to more challenging eight-membered rings. The field has matured to employ densely functionalized chiral porphyrin-based platforms that exhibit high enantio-, regio-, and stereoselectivity. Thus far the focus has largely been on cobalt-based systems, but interest has been growing for the past few years to expand the application of carbene radicals to other transition metals. This Perspective covers the advances made since 2011 and gives an overview on the coordination chemistry, reactivity, and catalytic application of carbene radical species using transition metal complexes and catalysts.

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Asymmetric Cyclopropanation of Olefins Catalyzed by a Chiral Cobalt(II) Porphyrin

Cited by 4 publications

References 12 publications

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group

Picket-fence ruthenium(II) phthalocyaninates bearing (1R,2S,5R)-menthoxy groups as prototype of chiral catalysts

Carbene Radicals in Transition-Metal-Catalyzed Reactions

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