Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

Trost, Barry M.; Tracy, Jacob S.; Saget, Tanguy

doi:10.1039/c8sc00147b

Cited by 42 publications

(18 citation statements)

References 67 publications

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“…In 2018, the Trost group reported a Zn‐ProPhenol catalyzed direct asymmetric amination reaction of unactivated cyclic aryl and vinyl ketones using di‐ tert ‐butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source (Scheme ) . There are only a few reports of direct enantioselective amination of unactivated ketones .…”

Section: Other Electrophilesmentioning

confidence: 99%

“…In 2018, the Trost group reported a Zn-ProPhenol catalyzed direct asymmetric amination reaction of unactivated cyclic aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source (Scheme 55). [96] There are only a few reports of direct enantioselective amination of unactivated ketones. [97] Both abranched (139) and unbranched (205) ketones were employed to construct tetrasubstituted and tri-substituted N-containing stereocenters.…”

Section: Di-tert-butyl Azodicarboxylatementioning

confidence: 99%

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Dinuclear Metal‐ProPhenol Catalysts: Development and Synthetic Applications

2019

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The ProPhenol ligand is a member of the chiral aza‐crown family that spontaneously forms a bimetallic complex upon treatment with alkyl metal reagents, such as Et2Zn and Bu2Mg. The resulting complex features Lewis acidic and Brønsted basic sites, enabling simultaneous activation of both nucleophile and electrophile in the same chiral environment. Since the initial report in 2000, metal‐ProPhenol catalysts have been used to facilitate a broad range of asymmetric transformations, including aldol, Mannich, and Henry reactions, as well as alkynylations and conjugation additions. By promoting such a diverse array of reactions, these complexes provide rapid and atom‐economical access to valuable complex building blocks. In this Review, we describe in detail the development and synthetic applications of these versatile catalysts with a special focus on recent efforts to improve reactivity and selectivity through ligand design and structural modification.

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Section: Other Electrophilesmentioning

confidence: 99%

Section: Di-tert-butyl Azodicarboxylatementioning

confidence: 99%

Dinuclear Metal‐ProPhenol Catalysts: Development and Synthetic Applications

2019

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“…82. a-Aminations of branched and unbranched aromatic ketones with ditert-butyl azodicarboxylate in the presence of (R,R)-ProPhenol (derivative) ligands [117].…”

Section: Hydrosilylations Of Carbonyl Compounds and Derivativesmentioning

confidence: 99%

Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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This review collects the recent advances in the field of enantioselective zinc-catalyzed transformations, covering the literature since the beginning of 2015, illustrating the power of chiral green zinc catalysts to promote all types of reactions. A range of highly enantioselective reactions have been developed in the last six years, including cycloadditions, alkynylation/allylation reactions of carbonyl compounds and derivatives, additions of diorganozincs to carbonyl compounds and derivatives, Mannich reactions, (nitro)aldol reactions, other 1,2-nucleophilic additions to carbonyl compounds and derivatives, Michael additions, Friedel-Crafts reactions, reductions, a-functionalizations of carbonyl compounds, ringopening reactions, epoxidations, halolactonizations, domino/tandem reactions and miscellaneous reactions.

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“…Im Jahr 2018 berichtete die Arbeitsgruppe von Trost über eine Zn‐ProPhenol‐katalysierte direkte asymmetrische Aminierungsreaktion nichtaktivierter cyclischer Aryl‐ und Vinylketone mittels Di‐ tert ‐butylazodicarboxylat als billiger und praktischer elektrophiler Stickstoffquelle (Schema ) . Nur wenige Berichte betreffen die direkte enantioselektive Aminierung nichtaktivierter Ketone .…”

Section: Andere Elektrophileunclassified

“…Im Jahr 2018 berichtete die Arbeitsgruppe von Trost über eine Zn-ProPhenol-katalysierte direkte asymmetrische Aminierungsreaktion nichtaktivierter cyclischer Aryl-und Vinylketone mittels Di-tert-butylazodicarboxylat als billiger und praktischer elektrophiler Stickstoffquelle (Schema 55). [96] Nur wenige Berichte betreffen die direkte enantioselektive Aminierung nichtaktivierter Ketone. [97] Sowohl a-verzweigte (139) als auch unverzweigte (205) Ketone wurden zur Bildung tetrasubstituierter und trisubstituierter N-haltiger Stereozentren eingesetzt.…”

Section: Di-tert-butylazodicarboxylatunclassified

Zweikernige Metall‐ProPhenol‐Katalysatoren: Entwicklung und Anwendungen in der Synthese

2019

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ProPhenol‐Moleküle gehören zur Gruppe der chiralen Azakronen‐Verbindungen und bilden bei Umsetzung mit Alkylmetall‐Reagenzien wie Et2Zn und Bu2Mg spontan einen bimetallischen Komplex. Dieser Komplex hat Lewis‐saure und Brønsted‐basische Reaktionszentren, die eine simultane Aktivierung eines Nukleophils und eines Elektrophils in derselben chiralen Umgebung erlauben. Seit dem ersten Bericht im Jahr 2000 haben Metall‐ProPhenol‐Katalysatoren eine große Bandbreite asymmetrischer Umwandlungen wie Aldol‐, Mannich‐ und Henry‐Reaktionen sowie Alkinylierungen und konjugierte Additionen ermöglicht. Aufgrund der vielfältigen Einsatzmöglichkeiten bei unterschiedlichen Reaktionen erlauben diese Komplexe einen schnellen und atomökonomischen Zugang zu wertvollen komplexen Baugruppen. In diesem Aufsatz beschreiben wir detailliert die Entwicklung und synthetischen Anwendungen dieser vielseitigen Katalysatoren, mit besonderem Blick auf kürzliche Bemühungen, Reaktivität und Selektivität durch Ligandendesign und strukturelle Veränderungen zu verbessern.

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Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

Abstract: A Zn–ProPhenol catalyzed direct amination of α-branched and unbranched ketones produces α-amino carbonyl and β-amino alcohol products.

Cited by 42 publications

References 67 publications

Dinuclear Metal‐ProPhenol Catalysts: Development and Synthetic Applications

Dinuclear Metal‐ProPhenol Catalysts: Development and Synthetic Applications

Recent developments in enantioselective zinc-catalyzed transformations

Zweikernige Metall‐ProPhenol‐Katalysatoren: Entwicklung und Anwendungen in der Synthese

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