Chromium(II)-catalyzed enantioselective arylation of ketones

Wang, Gang; Sun, Shutao; Mao, Ying; Xie, Zhibin; Liu, Lei

doi:10.3762/bjoc.12.275

Cited by 7 publications

(2 citation statements)

References 47 publications

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“…Monosubstituted derivatives are used in catalysis, [38][39][40][41] separation techniques, [35,[42][43][44] biomedical applications, [45][46][47] nanotechnologies [37,48] and sensors, [49] or as components of supramolecular assemblies. [50][51][52][53][54] The number of known monosubstituted CD derivatives is enormous and their listing would exceed the scope of this review. Thus, the aim of this paper is to provide a comprehensive view on the synthesis of monosubstituted derivatives suitable for further modifications.…”

Section: General Methods For Synthesis and Characterisation Of Monosumentioning

confidence: 99%

Monosubstituted Cyclodextrins as Precursors for Further Use

Řezanka

2016

Eur J Org Chem

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Cyclodextrin derivatives find use in a broad field of applications (e.g., nanomaterials, biomedical applications, catalysis, separation techniques, sensors etc.), with monosubstitution allowing cyclodextrins to be attached to various types of surfaces or for a new feature to be introduced onto a cyclodextrin skeleton (recognition, catalysis, …). Although an enormous number of monosubstituted cyclodextrin derivatives have been synthesised, this review focuses only on the synthesis of several interesting monosubstituted derivatives (allyl, cinnamyl, propargyl, formylmethyl, carboxymethyl, azido and amino) suitable for further modifications. These derivatives allow the synthesis of an unlimited number of desired cyclodextrin derivatives. Using a cyclodextrin derivative already monosubstituted with a suitable functional group is much easier than the optimisation of monosubstitution for every new cyclodextrin derivative desired.

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Section: General Methods For Synthesis and Characterisation Of Monosumentioning

confidence: 99%

Monosubstituted Cyclodextrins as Precursors for Further Use

Řezanka

2016

Eur J Org Chem

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“…With the success of secondary alkyl radical-involved asymmetric additions to aldehydes, we anticipate that ketones might act as suitable substrates in these catalytic systems. Indeed, elegant reports from the Sigman, Chen, and Connell groups described the Cr-catalyzed asymmetric allylation or propargylation of ketones to afford enantioenriched tertiary alcohols. , However, these studies predominantly focused on using primary alkyl halides for single-stereocenter construction. Notably, secondary alkyl electrophiles are easily accessible, and their reaction with ketones provides efficient access to tertiary alcohols bearing vicinal stereocenters.…”

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confidence: 99%

Cr-Catalyzed Regio-, Diastereo-, and Enantioselective Reductive Couplings of Ketones and Propargyl Halides

et al. 2023

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Enantioconvergent reductive couplings of racemic alkyl halides with carbonyl compounds provide efficient access to valuable chiral alcohols, especially those bearing vicinal stereocenters. However, limited success has been achieved due to the challenging reactivity and stereoselectivity control. Herein, we developed the Cr-catalyzed asymmetric reductive coupling of racemic propargylic chlorides and ketones, affording valuable chiral tertiary alcohols bearing vicinal stereocenters. These reactions proceed efficiently under mild conditions in a radical−polar crossover manner with good regio-, diastereo-, and enantioselectivity control. Preliminary mechanistic studies, including radical trapping, nonlinear effect, and UV−vis spectroscopy, provide insights into the radical-involved catalytic cycle. DFT calculations suggest that the regio-and stereoselectivity are determined by the Zimmerman−Traxler-type ketone addition transition states under Curtin−Hammett conditions.

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Nickel‐Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes

Zhu

Xiao

et al. 2022

Angewandte Chemie

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Enantioenriched alcohols comprise much of the framework of organic molecules. Here, we first report that chiral nickel complexes can catalyze the intermolecular enantioselective addition of aryl iodides across aldehydes to provide diverse optically active secondary alcohols using zinc metal as the reducing agent. This method shows a broad substrate scope under mild reaction conditions and precludes the traditional strategy through the pre-generation of organometallic reagents. Mechanistic studies indicate that an in situ formed arylnickel, instead of an arylzinc, adds efficiently to aldehydes, forming a new CÀ C bond and a chiral nickel alkoxide that may be turned over by zinc powder.

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Chromium(II)-catalyzed enantioselective arylation of ketones

Cited by 7 publications

References 47 publications

Monosubstituted Cyclodextrins as Precursors for Further Use

Monosubstituted Cyclodextrins as Precursors for Further Use

Cr-Catalyzed Regio-, Diastereo-, and Enantioselective Reductive Couplings of Ketones and Propargyl Halides

Nickel‐Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes

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