Organocatalytic Regio‐ and Enantioselective <i>N</i>‐Alkylation of Isoxazol‐5‐ones

Liu, Meiwen; Qian, Chenxiao; Li, Pengfei

doi:10.1002/ejoc.202101415

Cited by 6 publications

(2 citation statements)

References 57 publications

(12 reference statements)

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“…Where additional comparison data is available, several other studies involving imine-type electrophiles (C=N-R) have shown the importance of including TCYP in a catalyst evaluation despite the structural similarities with TRIP. [32][33][34][35][36][37][38][39][40][41] By performing this type of analysis with similarly related electrophiles, azo compounds, [42][43][44][45][46] precedent shows TCYP to be a top performer. Continued expansion of this comparative analysis demonstrates TCYP to be effective in condensation, 47,48 halogenation [49][50][51][52] and organometallic reactions.…”

Section: Inverse Catalyst Designmentioning

confidence: 99%

A Statistical Modeling Approach to Catalyst Generality Assessment in Enantioselective Synthesis

Lai

Betinol

et al. 2022

Preprint

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Selecting the optimal catalyst to impart high levels of enantioselectivity in a new transformation is challenging because the ideal molecular requirements of the catalyst for one reaction do not always simply translate to another. In these reaction scenarios practitioners typically use the most general catalyst structure as a starting point for optimization. However, for many reaction systems and catalyst chemotypes the most general catalyst structure may be largely unknown presenting a significant limitation in catalyst application to new reaction space. Herein, we demonstrate that comprehensive statistical models can be applied to identify the most general catalyst for many chemical systems. These inclusive statistical models that encompass many reaction types can provide information about the relevant structural requirements necessary for high enantioselectivity across a broad reaction range. By validating this approach on diverse regions of organocatalyzed reaction space we discovered structurally distinct catalysts can in some cases provide similar levels of enantioselectivity. The second curious finding determined that the best and most popular catalyst systems may not be equivalent. Validation of this approach on a multi-catalytic dearomatization reaction resulted in the discovery that our general catalyst findings allowed for streamlined reaction development for highly complex transformations.

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Section: Inverse Catalyst Designmentioning

confidence: 99%

A Statistical Modeling Approach to Catalyst Generality Assessment in Enantioselective Synthesis

Lai

Betinol

et al. 2022

Preprint

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“…Based on our previous work on the reactions of functionalized propargylic alcohols, 11 b ,12 a ,13 c – f we have successfully developed diverse organocatalytic reactions of α-(3-isoindolinonyl) propargylic alcohols, 15 a,b which in situ generated β,γ-alkynyl-α-imines under acidic conditions. 16 As a continuation of our effort in organocatalytic reactions of propargylic alcohols, we have a high motivation to explore reactions of α-(3-isoindolinonyl) propargylic alcohols with challenges in terms of regio- and stereoselectivities. Here, we reported a CPA-catalyzed regio- and enantioselective reaction of 2-indolylnaphthalenols with α-(3-isoindolinonyl) propargylic alcohols (Scheme 1B).…”

Section: Introductionmentioning

confidence: 99%

Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality

et al. 2023

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Catalytic Asymmetric Chlorination of Isoxazolinones

et al. 2022

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Organic compounds featuring a chlorine substituted stereocenter are frequently found in nature and are interesting for pharmaceutical applications and as synthetic building blocks. Catalytic methods to generate such stereocenters by C,H bond functionalization are still relatively rare. Here we report the first catalytic asymmetric chlorination of isoxazolinones, a synthetically and biologically interesting class of heterocycles, which can be considered as precursors for β-aminoacids. The title reaction was catalyzed with high enantioselectivity by a planar chiral ferrocene based palladacycle in high to excellent yields. It is showcased that the products are valuable for post-synthetic transformations. An S N 2 reaction proceeded with smooth inversion of the absolute configuration. The substitution product could then be transformed into an α-azido β-aminoacid derivative via a reductive, diastereoselective ring opening.

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Organocatalytic Regio‐ and Enantioselective N‐Alkylation of Isoxazol‐5‐ones

Cited by 6 publications

References 57 publications

A Statistical Modeling Approach to Catalyst Generality Assessment in Enantioselective Synthesis

A Statistical Modeling Approach to Catalyst Generality Assessment in Enantioselective Synthesis

Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality

Catalytic Asymmetric Chlorination of Isoxazolinones

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