Enantioselective Fluorination of β‐Ketoamides Catalyzed by Ar‐BINMOL‐derived SalanCopper Complex

Zheng, Long-Sheng; Wei, Yuanyuan; Jiang, Kezhi; Deng, Yuan; Zheng, Zhan‐Jiang; Xu, Li‐Wen

doi:10.1002/adsc.201400603

Cited by 37 publications

(15 citation statements)

References 80 publications

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“…If we keep talking about copper, asymmetric fluorination of methyl 1-indanone-2-carboxylate (12) catalyzed by the Cu(II)/Ar-BINMOL-derived salan system (Ar-BINMOL = 1,1 -binaphthalene -2-α-arylmethanol-2 -ol) (3, Figure 2) gave 82% ee and 99% yield (entry 10, Table 1) [47]. Only β-keto ester 12 (Scheme 1) was tested, however, these conditions were applied with great success to a series of β-keto amides.…”

Section: Metal-catalyzed Methodsmentioning

confidence: 99%

Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review

Granados

Vallribera

2020

Molecules

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In this review, recent advances over the past decade in the preparation of fluorinated stereogenic quaternary centers on β-keto esters compounds are analyzed. Since the incorporation of fluorine and fluorinated groups is of special interest in pharmaceutical chemistry, a range of metal-catalyzed and organocatalyzed methods have been developed. Herein, we review the enantioselective fluorination, trifluoromethylation and trifluoromethylthiolation of 3-oxo esters. The scope, the induction of enantioselectivity and mechanistic investigations are presented.

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Section: Metal-catalyzed Methodsmentioning

confidence: 99%

Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review

Granados

Vallribera

2020

Molecules

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“…Xu and coworkers utilized Cu(II) complexes of salen-type ligands derived from axially chiral 1,1'binaphthalenealdehydes and (1S,2S)-1,2-diaminocyclohexane for the enantioselective fluorination of N-substituted and N,N-disubstituted cyclic β-ketoamides with a five-or six-membered ring (19 examples, 99 % yield, 80-99 % ee). [35] Kim and Kwon utilized the Pd(II) complex of a BINAP-type ligand and a sterically hindered amine base. Various N-substituted cyclic βketoamides with a five-or six-membered ring were transformed successfully (Scheme 7).…”

Section: Fluorination Of Enolates Of β-Keto Esters and Related Compoundsmentioning

confidence: 99%

Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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In memory of Ferenc FülöpAs a consequence of the ever-increasing relevance of fluorinated drugs in medicinal chemistry, organofluorine chemistry has become a hot topic research area during the last decade. Asymmetric carbon-fluorine bond-forming reactions have enormously developed in recent years with considerable findings related to novel reactions and synthetic approaches. These new synthetic efforts have contributed to the access to a growing number of fluorinated molecules and complex natural or synthetic products of high relevance in medicinal chemistry and drug research. Illustrative examples of novel synthetic methodologies, including organocatalytic processes, asymmetric syntheses or phase-transfer catalytic methods for the enantioselective incorporation of fluorine atom(s) into versatile molecular entities, are covered in the current Review, focusing on main contributions of the last ten years.

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“…developed a mild protocol of DMAP‐catalyzed aminolysis of β ‐keto esters 22 to various β ‐keto amides 23 in good yields (Scheme 6a). Using molecular sieves (3 Å MS) as the catalyst, the reaction can proceed at lower temperatures (75–80 °C) [38] . Later on, Witzeman et al [39] .…”

Section: Synthesis Of β‐Keto Amidesmentioning

confidence: 99%

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

Zheng

et al. 2021

Eur J Org Chem

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β‐Keto amides are a versatile class of compounds that find wide applications in organic chemistry owing to the juxtaposition of multiple reaction sites within their molecular structures. Due to the importance of β‐keto amides in modern organic chemistry, numerous novel preparation methods, synthetic applications and unprecedented reactivities have been recorded over the past decade. Taking advantage of transition‐metal‐catalysis and organocatalysis, β‐keto amides have emerged into a jack‐of‐all‐trades building block for many stereoselective or tandemized multicomponent reactions. But so far, no reviews have been documented on these recent achievements with β‐keto amides. Our Review aims to provide a thorough summary regarding: (a) the synthesis of β‐keto amides, (b) the reactivities of β‐keto amides, (c) the synthetic applications of β‐keto amides in various important heterocyclic compounds, and (d) the coordination of β‐keto amides with main group elements and transition metals and the relevant applications.

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Enantioselective Fluorination of β‐Ketoamides Catalyzed by Ar‐BINMOL‐derived SalanCopper Complex

Cited by 37 publications

References 80 publications

Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review

Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review

Asymmetric Methods for Carbon‐Fluorine Bond Formation

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

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