New chiral ferrocene/indole-based diphosphine ligands for Rh-catalyzed asymmetric hydrogenation of functionalized olefins

Abbas, Zaheer; Hu, Xiang-Ping; Ali, Aijaz; Xu, Youwei

doi:10.1016/j.tetlet.2020.151860

Cited by 7 publications

(4 citation statements)

References 48 publications

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“…Industrial hydrogenation is known to be based on heterogeneous catalysts, but another way of hydrogenation of olefins builds upon chiral ferrocene/indole-based diphosphine ligands, resulting in high yields and enantioselectivity. As reported by Z. Abbas et al, ferrocenyl indoles 60 exhibited a superior catalytic activity in reactions of asymmetric hydrogenation of α-enamides 59 (Scheme 11) [41]. The product (S)-61 is formed with high enantioselectivity (up to 97% ee), the yield is not lower than 88%.…”

Section: Asymmetric Hydrogenationmentioning

confidence: 61%

Advanced Application of Planar Chiral Heterocyclic Ferrocenes

et al. 2022

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Section: Asymmetric Hydrogenationmentioning

confidence: 61%

Advanced Application of Planar Chiral Heterocyclic Ferrocenes

et al. 2022

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“…[24] Peracetylation with excess acetyl chloride then gave 42. Selective ester hydrolysis gave 43 [25,26] and then a modified Moffat oxidation gave aldehyde 36.…”

Section: Resultsmentioning

confidence: 99%

Reductive Release from a Hybrid PKS‐NRPS during the Biosynthesis of Pyrichalasin H

Heinemann,

Zhang,

Cox

2023

Chemistry A European J

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Three central steps during the biosynthesis of cytochalasan precursors, including reductive release, Knoevenagel cyclisation and Diels Alder cyclisation are not yet understood at a detailed molecular level. In this work we investigated the reductive release step catalysed by a hybrid polyketide synthase non‐ribosomal peptide synthetase (PKS‐NRPS) from the pyrichalasin H pathway. Synthetic thiolesters were used as substrate mimics for in vitro studies with the isolated reduction (R) and holo‐thiolation (T) domains of the PKS‐NRPS hybrid PyiS. These assays demonstrate that the PyiS R‐domain mainly catalyses an NADPH‐dependent reductive release of an aldehyde intermediate that quickly undergoes spontaneous Knoevenagel cyclisation. The R‐domain can only process substrates that are covalently bound to the phosphopantetheine thiol of the upstream T‐domain, but it shows little selectivity for the polyketide.

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“…The main features of this new class of chiral diphosphines are their easy accessibility and facile derivatization, together with a remarkable air-and moisture-stability. The corresponding Rh(I) complexes achieved outstanding enantioselectivity in the asymmetric hydrogenation of functionalized olefins, with up to >99% yields and 98% ees [68].…”

Section: Cyclopentadienyl-and Ferrocenyl-based Ligandsmentioning

confidence: 99%

Rh(I) Complexes in Catalysis: A Five-Year Trend

et al. 2021

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Rhodium is one of the most used metals in catalysis both in laboratory reactions and industrial processes. Despite the extensive exploration on “classical” ligands carried out during the past decades in the field of rhodium-catalyzed reactions, such as phosphines, and other common types of ligands including N-heterocyclic carbenes, ferrocenes, cyclopentadienyl anion and pentamethylcyclopentadienyl derivatives, etc., there is still lively research activity on this topic, with considerable efforts being made toward the synthesis of new preformed rhodium catalysts that can be both efficient and selective. Although the “golden age” of homogeneous catalysis might seem over, there is still plenty of room for improvement, especially from the point of view of a more sustainable chemistry. In this review, temporally restricted to the analysis of literature during the past five years (2015–2020), the latest findings and trends in the synthesis and applications of Rh(I) complexes to catalysis will be presented. From the analysis of the most recent literature, it seems clear that rhodium-catalyzed processes still represent a stimulating challenge for the metalloorganic chemist that is far from being over.

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New chiral ferrocene/indole-based diphosphine ligands for Rh-catalyzed asymmetric hydrogenation of functionalized olefins

Cited by 7 publications

References 48 publications

Advanced Application of Planar Chiral Heterocyclic Ferrocenes

Advanced Application of Planar Chiral Heterocyclic Ferrocenes

Reductive Release from a Hybrid PKS‐NRPS during the Biosynthesis of Pyrichalasin H

Rh(I) Complexes in Catalysis: A Five-Year Trend

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