Enantioselective Synthesis of Polycyclic γ-Lactams with Multiple Chiral Carbon Centers via Ni(0)-Catalyzed Asymmetric Carbonylative Cycloadditions without Stirring

Ashida, Keita; Hoshimoto, Yoichi; Tohnai, Norimitsu; Scott, David E.; Ohashi, Masato; Imaizumi, Hanae; Tsuchiya, Yuichiro; Ogoshi, Sensuke

doi:10.1021/jacs.9b12493

Cited by 56 publications

(27 citation statements)

References 77 publications

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“…When tetrafluoroethene bearing no hydrogen atom was subjected together with silane, alkylation of imines took place 47 . Moreover, Ogoshi's group recently used carbonyl insertion to interrupt the facile β-H elimination; displacement of the nickel from the nickellacycle intermediate provides saturated γ-lactams 59,60 .…”

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confidence: 99%

Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Yan

et al. 2021

Nat Commun

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Hydroalkylation, the direct addition of a C(sp3)–H bond across an olefin, is a desirable strategy to produce valuable, complex structural motifs in functional materials, pharmaceuticals, and natural products. Herein, we report a reliable method for accessing α-branched amines via nickel-catalyzed hydroalkylation reactions. Specifically, by using bis(cyclooctadiene)nickel (Ni(cod)2) together with a phosphine ligand, we achieved a formal C(sp3)–H bond insertion reaction between olefins and N-sulfonyl amines without the need for an external hydride source. The amine not only provides the alkyl motif but also delivers hydride to the olefin by means of a nickel-engaged β–hydride elimination/reductive elimination process. This method provides a platform for constructing chiral α-branched amines by using a P-chiral ligand, demonstrating its potential utility in organic synthesis. Notably, a sulfonamidyl boronate complex formed in situ under basic conditions promotes ring-opening of the azanickellacycle reaction intermediate, leading to a significant improvement of the catalytic efficiency.

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confidence: 99%

Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Yan

et al. 2021

Nat Commun

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“…However, the aforementioned canonical SLs analogues named eudesmanestrigolactones generate percentages of 80-100% in the range 0.1-100 µM, as well as the well-known synthetic analogue GR24 [57]. Other examples of active canonical analogues have been published [77,78], so deeper studies should be carried out to obtain more substantiated conclusions on possible structural advantages for the germination of O. cumana in regard to canonical/non-canonical structures.…”

Section: Germination Activity On Parasitic Plant Seeds and Structure-activity Relationshipsmentioning

confidence: 99%

Allelopathic Activity of Strigolactones on the Germination of Parasitic Plants and Arbuscular Mycorrhizal Fungi Growth

et al. 2021

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Strigolactones (SLs) are a prime example of allelochemicals, promoting parasitic plant germination and certain hyphal branching factors associated to the growth of symbiotic arbuscular mycorrhizal fungi (AMF). However, the study of SLs is complex, and various issues have yet to be studied in depth. This review intends to provide an overview of the works that have been conducted on the identification, isolation, and evaluation of the allelopathic activity of natural canonical and non-canonical SLs on parasitic weeds and AMF growth. These topics were related with their application in agriculture through trap crops, suicidal germination or intercropping strategies. The high applicability of SLs in agriculture, for example, as preventing herbicides for parasitic weed control, has increased the interest for these compounds and the number of research articles published. This review updates and discusses the last findings in this field, with special emphasis in the results published since 2015, using tables and graphs to summarize and discuss that information. The promising results and conclusions obtained from the bioassays herein presented provide a good reason to encourage and support further research works on these natural products, which must also consider the disadvantages or current limitations that SLs present.

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“…128 Enantioselective synthesis of poly cyclic γ-lactam was reported by Tohnai, Ogoshi, and co-workers. 129 Within the oxidative cyclization on Ni(0), enantioselectivity for carbon atoms of the γ-lactams was regulated. Morofuji/Kano team demonstrated photocatalytically driven C-H alkylation of heteroarenes by alkylsilicates having C,O-bidentate ligands under acidic conditions.…”

Section: Molecular Machine and Molecular Functionmentioning

confidence: 99%

Nanoarchitectonics for Coordination Asymmetry and Related Chemistry

Ariga

Shionoya

2020

Bulletin of the Chemical Society of Japan

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Nanoarchitectonics is a concept envisioned to produce functional materials from nanoscale units through fusion of nanotechnology with other scientific disciplines. For component selection, coordination complexes with metallic elements have a wider variety of element selection because metallic elements cover ca. 80% of the periodic table of the elements. Application of nanoarchitectonics approaches to coordination chemistry leads to huge expansion of this concept to a much wider range of elements. Especially, coordination asymmetry strategy architects asymmetrical and/or chiral structures and/or electronic states through formation of metal coordination complexes, leading to functional material systems in certain anisotropy and selectivity. This review article presents expansion of the nanoarchitectonics concept to coordination asymmetry through collecting recent examples in the field of coordination asymmetry. Introduced examples are classified into several categories from various viewpoints: (i) basic molecular and material designs; (ii) specific features depending on interfacial media, space and contact with bio-functions; (iii) functions; (iv) supporting techniques such as analyses and theory.

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Enantioselective Synthesis of Polycyclic γ-Lactams with Multiple Chiral Carbon Centers via Ni(0)-Catalyzed Asymmetric Carbonylative Cycloadditions without Stirring

Cited by 56 publications

References 77 publications

Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Allelopathic Activity of Strigolactones on the Germination of Parasitic Plants and Arbuscular Mycorrhizal Fungi Growth

Nanoarchitectonics for Coordination Asymmetry and Related Chemistry

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