Iridium-Catalyzed Enantioselective Ring Opening of Alkenyl Oxiranes by Unactivated Carboxylic Acids

Pandit, Soumen; Adhikari, Amit Singh; Majumdar, Nilanjana

doi:10.1021/acs.orglett.2c02919

Cited by 5 publications

(3 citation statements)

References 64 publications

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“…The relationship of OH-7 and OH-8 was assigned to be erythro by comparison of NMR data with those for triharzianin C [ 19 ]. Although the chemical shifts of C-1, C-2, and C-3 in 2 were the same as those of ( S )-but-3-ene-1,2-diol [ 23 ], the relative configuration of OH-2 could not be confirmed due to the existence of only one chiral carbon atom (C-2) in this moiety. Thus, compound 2 was named (3 E ,5 E ,11 E )-trideca-3,5,11-trien-1,2,7,8-tetraol, and its structural formula was HOCH 2 CH(OH)CH=CHCH=CHCH(OH)CH(OH)CH 2 CH 2 CH=CHCH 3 .…”

Section: Resultsmentioning

confidence: 99%

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

Shi,

Yin,

2023

Marine Drugs

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Six new lipids, trichoderols B-G (1–6), along with a known one, triharzianin B (7), were isolated from the culture of Trichoderma sp. Z43 obtained from the surface of the marine brown alga Dictyopteris divaricata. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1–7 were assayed for inhibiting the growth of three phytopathogenic fungi (Fusarium graminearum, Gaeumannomyces graminis, and Glomerella cingulata), four marine phytoplankton species (Amphidinium carterae, Heterocapsa circularisquama, Heterosigma akashiwo, and Prorocentrum donghaiense), and one marine zooplankton (Artemia salina). Compounds 1, 4, and 7 exhibited weak antifungal activities against three phytopathogenic fungi tested with MIC ≥ 64 μg/mL. All compounds displayed moderate antimicroalgal activity with IC50 ≥ 15 μg/mL and low toxicity to the brine shrimp Artemia salina.

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Section: Resultsmentioning

confidence: 99%

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

Shi,

Yin,

2023

Marine Drugs

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“…In 2022, Majumdar et al had described the iridium-catalyzed reaction of racemic vinyl oxiranes with carboxylic acids by employing the (S)-configured BINOL-phosphoramidite-olefin L35 as ligand (Scheme 68). [104] The reaction of racemic vinyl oxirane rac-97 (1.5 equiv) with benzoic acid (1 equiv) in the presence of [Ir(COD)Cl] 2 (1 mol %) and L35 (4 mol %) in THF at room temperature afforded the allylic benzoate 145 a with 58 % ee. Surprisingly, the ee-value of 145 a increased to 80 % through the application of four equivalents of the vinyl oxirane.…”

Section: Iridium-catalyzed Dynamic Kinetic Asymmetric Transformation ...mentioning

confidence: 99%

Palladium‐ and Iridium‐Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles

Gais

2022

Eur J Org Chem

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Allylic oxygen compounds (AOCs) are an important class of versatile building blocks in natural and non‐natural product synthesis. Catalytic in‐situ deracemization is an attractive means for their enantioselective synthesis. Particularly attractive is the deracemization of AOCs through transition metal‐catalyzed dynamic kinetic asymmetric transformation (DYKAT) with oxygen nucleophiles (ONus). This review describes pertinent aspects of the palladium‐catalyzed DYKAT of racemic allylic carboxylates, vinyl oxiranes and vinyl dioxolanones with carboxylates, hydrogen carbonate, alcohols, phenols, oximes, diosphenols and water and the iridium‐catalyzed DYKAT of racemic allylic alcohols, imidates and carboxylates with alcohols and carboxylic acids. Included in the discussion is the palladium‐catalyzed desymmetrization of meso‐cycloalkene bis(carboxylates) with hydrogen carbonate. While Trost's bisphosphinobenzamides, Zhou's spiro‐phosphoramidite and Feringa's BINOL‐phosphoramidite are highly efficient ligands in palladium‐catalyzed DYKAT, Carreira‐Dorta's BINOL‐phosphoramidite‐olefin is an excellent ligand in iridium‐catalyzed DYKAT. This review also discusses mechanistic and structural aspects of η3‐allylpalladium‐bisphosphinobenzamide and η3‐allyliridium‐BINOL‐phosphoramidite‐olefin complexes and of the corresponding catalysts.

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“…Vinylcyclopropanes are easy to access and, therefore, highly useful substrates for important synthetic transformations. − Carboxylic acids are ubiquitous, commercially abundant, structurally diverse, inexpensive, stable compounds and, therefore, quite useful substrates for asymmetric transformations . Development of catalytic asymmetric strategies involving vinylcyclopropanes and carboxylic acids for the synthesis of a valuable compound class would be highly desirable.…”

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confidence: 99%

Iridium-Catalyzed Enantioselective Allylic Substitution of Vinylcyclopropanes by Carboxylic Acids

et al. 2023

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An efficient method for a highly regio- and enantioselective allylic substitution of vinylcyclopropanes using carboxylic acids as oxygen nucleophile via iridium catalysis has been developed. This represents a highly atom-economic approach for the synthesis of synthetically useful chiral building blocks in high yields. The practical utility of this method is demonstrated by the application of the products in useful transformations.

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Iridium-Catalyzed Enantioselective Ring Opening of Alkenyl Oxiranes by Unactivated Carboxylic Acids

Cited by 5 publications

References 64 publications

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

Palladium‐ and Iridium‐Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles

Iridium-Catalyzed Enantioselective Allylic Substitution of Vinylcyclopropanes by Carboxylic Acids

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