Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand

Wu, Linglin; Zatolochnaya, Olga V.; Qu, Bo; Wells, Lucille A.; Kozlowski, Marisa C.; Senanayake, Chris H.; Song, Jinhua J.; Zhang, Yongda

doi:10.1021/acs.orglett.9b03328

Cited by 28 publications

(16 citation statements)

References 20 publications

(21 reference statements)

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“…It was only recently that Zhang and Wu identified a newly developed Piv Zphos ligand as a highly effective chiral ligand for the Cu‐catalyzed aminoboration of ( E )‐styrenes (Scheme 9). [42] Under the optimized conditions, all β‐aminoalkylboronate products were obtained with a syn diastereochemistry in ≥92% ee (up to 99% ee).…”

Section: Methods For the Synthesis Of β‐Aminoalkylboronic Acid Derivativesmentioning

confidence: 94%

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Hall

2020

Adv Synth Catal

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α‐Aminoalkylboronic acids display a distinct role in medicinal chemistry, and their utility has been demonstrated by the successful commercialization of three drugs: bortezomib, ixazomib, and vaborbactam. Just as α‐aminoalkylboronic acids are a bioisostere of α‐amino acids, β‐aminoalkylboronates are a bona fide bioisostere of β‐amino acids, thus they also hold promising potential in drug discovery. Moreover, β‐aminoalkylboronates are versatile synthetic intermediates that are amenable to many of the established C−B bond derivatization reactions of chiral optically enriched alkylboronates, leading to the stereocontrolled preparation of valued classes of products such as β‐amino alcohols, 1,2‐diamines, and hemiboronic acid heterocycles. In addition, β‐aminoalkylboronates were shown to act as catalysts in certain organic reactions. This review presents an overview of the strengths and limitations of current preparative methods to access β‐aminoalkylboronic acid derivatives stereoselectively with various substitution patterns. Strategically, several disconnections can be exploited to establish both functional groups. Some of the key methods include the classical Matteson asymmetric homologation chemistry, transition metal‐catalyzed aminoboration of alkenes and formal hydroboration of enamine derivatives, nucleophilic additions of boryl‐substituted carbanions onto N‐functionalized imines, borylative ring openings of aziridines, and functionalization of alpha‐boryl aldehydes.

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Section: Methods For the Synthesis Of β‐Aminoalkylboronic Acid Derivativesmentioning

confidence: 94%

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Hall

2020

Adv Synth Catal

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“…[306] For nearly all reactions shown in Scheme 70, enantioselective modifications of the protocols employing chiral diphosphine ligands were also reported. [303,305,307,308] Other electrophilic reagents could be used in the Cucatalyzed borylation of alkenes, including diazo compounds (hydrazinoboration, Scheme 71, A), [309] ylpiperidin-1-yl)oxyl) (TEMPO) as an oxidant (oxyboration, B), [310] or stannanes (borostanation, C). [311] Engle and co-workers reported AQ-directed Pd-catalyzed aminoboration of alkenes which is very similar to their approach to the carboboration (Scheme 72, cf Scheme 65).…”

Section: Alkene Heteraborationsmentioning

confidence: 99%

Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

Volochnyuk

Gorlova

Grygorenko

2021

Chemistry A European J

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This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications of the title compounds in the design of boron-containing drugs are surveyed, with special emphasis on α-amino boronic derivatives. A general overview of saturated boronic compounds as modern tools to construct C(sp 3 )À C and C(sp 3 )-heteroatom bonds is given, including recent developments in the Suzuki-Miyaura and Chan-Lam cross-couplings, single-electron-transfer processes including metallo-and organocatalytic photoredox reactions, and transformations of boron "ate" complexes. Finally, an attempt to summarize the current state of the art in the synthesis of saturated boronic acids, boronates, and trifluoroborates is made, with a brief mention of the "classical" methods (transmetallation of organolithium/magnesium reagents with boron species, anti-Markovnikov hydroboration of alkenes, and the modification of alkenyl boron compounds) and a special focus on recent methodologies (boronation of alkyl (pseudo)halides, derivatives of carboxylic acids, alcohols, and primary amines, boronative CÀ H activation, novel approaches to alkene hydroboration, and 1,2-metallate-type rearrangements).

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“…The application of allylic electrophiles to three-component reactions gained similar success. − For example, Hoveyda and co-workers reported a copper-catalyzed asymmetric allyl–allyl coupling reaction where the allylcopper complex XXI derived from allenes could react with γ-substituted allylic phosphates with high enantioselectivity and good γ-selectivity of allylic electrophiles . In addition, heteroatom electrophiles such as O -benzoyl-hydroxylamine 19 and stannyl ether 20 underwent borylative substitution equally well. − …”

Section: Three-component Reactionsmentioning

confidence: 99%

Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates

Xue

Oestreich

2020

ACS Cent. Sci.

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Catalytic asymmetric C–C bond formation with alkylcopper intermediates as carbon nucleophiles is now textbook chemistry. Related chemistry with boron and silicon nucleophiles where the boryl- and accordingly silylcopper intermediates are catalytically regenerated from bench-stable pronucleophiles had been underdeveloped for years or did not even exist until recently. Over the past decade, asymmetric copper catalysis employing those main-group elements as nucleophiles rapidly transformed into a huge field in its own right with an impressive breadth of enantioselective C–B and C–Si bond-forming reactions, respectively. Its current state of the art does not have to shy away from comparison with that of boron’s and silicon’s common neighbor in the periodic table, carbon. This Outlook is not meant to be a detailed summary of those manifold advances. It rather aims at providing a brief conceptual summary of what forms the basis of the latest exciting progress, especially in the area of three-component reactions and cross-coupling reactions.

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Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with ^pivZPhos as the Ligand

Cited by 28 publications

References 20 publications

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates

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