Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric Synthesis

Marshall, James A.

doi:10.1021/cr950037f

Cited by 415 publications

(153 citation statements)

References 59 publications

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“…106 The catalytic activity for the reaction of benzaldehyde with allyltrimethylsilane under solvent-free conditions was compared with other copper catalysts (Eq. 26).…”

Section: Catalysis Of Scmentioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

143

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This account reviews a novel approach to designing high-performance heterogeneous metal catalysts using hydroxyapatites, montmorillonites, and hydrotalcites as macroligands of active metal species for aerobic alcohol oxidations, carbon-carbon bond formations, and one-pot syntheses. The catalytic systems using the above heterogeneous catalysts offer significant benefits in achieving environmentally friendly organic syntheses aiming towards Green and Sustainable Chemistry. Furthermore, the present preparation method for the immobilization of metal species is strikingly simple and allows a strong protocol for creating various nanostructured and functionalized heterogeneous catalysts.Green and Sustainable Chemistry (GSC) is a revolutionary philosophy that aims to bring about a sustainable society by improvement of the safety and environmental aspects of chemical processes and reduction of the risks of chemical products to people and the environment.1 The emphasis is on eliminating waste at the source-primary pollution prevention-rather than finding incremental end-of-pipe solutions. This concept aims to solve the societal problems of the last century associated with the mass production and consumption of materials, and plays a prime role in providing a venous function in society, encouraging reuse and circulation of resources.One of the powerful solutions in the move toward GSC is the replacement of traditional synthetic methods using harmful stoichiometric reagents that produce vast amounts of waste with cleaner and simple catalytic alternatives with high atom efficiency 1a and low E-factors. 1b Catalytic chemistry, therefore, is of ever-increasing importance because catalysis is a key element in material transformations at atomic and molecular levels, which are an essential realm of chemistry and chemical processes.Our approach to GSC is to develop a highly functionalized heterogeneous metal catalyst based on the unique characteristics of natural layered inorganic materials such as hydroxyapatite, montmorillonite, and hydrotalcite, by using them as macroligands for metal species.2 We consider the above inorganic materials to be advanced nano-scaled catalyst supports allowing for the control of the location of catalytically active metal species, which can be found, for example, on the surface, among the layers, or in the interlayer space. Furthermore, these materials are capable of creating catalytically active metal species responsible for targeted organic transformations involving monomers, chain-like species or giant clusters. The creation of well-defined active metal sites on a solid surface, as characterized by X-ray absorption spectroscopy, not only opens up an avenue to materials that boost catalytic performance, but also aids in the understanding of the molecular basis of heterogeneous catalysis. Another advantage of these catalysts is the possibility of a one-pot synthesis based on a cooperative action by several immobilized active species on the solid surface as multifunctional catalysts. The target react...

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“…106 The catalytic activity for the reaction of benzaldehyde with allyltrimethylsilane under solvent-free conditions was compared with other copper catalysts (Eq. 26).…”

Section: Catalysis Of Scmentioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

143

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“…[1][2][3] Die hinreichende chemische Stabilität dieser sekundären Zinnverbindungen wird für gewöhnlich durch einen Sauerstoffsubstituenten am a- [4] oder g-Kohlenstoffatom [5] gewährleistet, während allylische Systeme ohne jedwede Substitution durch ein Heteroatom wegen ihrer ausgeprägten Tendenz zur 1,3-Zinnverschiebung oder gar Zersetzung als empfindlich gelten. [1] Das Fehlen milder Verfahren zur Synthese dieser schwer zu fassenden nur-Kohlenstoff-substituierten Allylstannane mag die Fortentwicklung ihrer Chemie bislang vereitelt haben.…”

Section: Eric S Schmidtmann Und Martin Oestreich*unclassified

“…Das macht den ansonsten erforderlichen Einsatz stöchiometrischer Mengen an Kupfer überflüssig. So verläuft die allylische Substitution von Allylbenzoaten in Gegenwart von Kupfer(i)-iodid als Katalysator mit (Me 2 PhSi) 2 Zn als Siliciumquelle reibungslos.…”

Section: Eric S Schmidtmann Und Martin Oestreich*unclassified

Enantiospezifische Synthese und Allylierung ausschließlich Kohlenstoff‐substituierter, α‐chiraler Allylstannane

Schmidtmann

Oestreich

2009

Angewandte Chemie

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“…[32] PrØvost et al fanden bereits 1950, dass Allen-Grignard-Reagentien an Carbonyladditionen teilnehmen, wobei Gemische von b-Acetylen-und aAllencarbinolen entstehen; hierfür wurde der Begriff "Propargylumlagerung" geprägt. [33a,b] Mukaiyama (1981), dass Stannane, die in situ aus Propargyliodiden und Zinnchlorid erzeugt werden, bei der Reaktion mit Aldehyden Gemische von b-Acetylen-und a-Allencarbinolen liefern.…”

Section: Hydrierende Carbonylpropargylierung Mit 13-eninen Als Propaunclassified

Katalytische Carbonyladdition durch Transferhydrierung: weg von vorab gebildeten Organometallreagentien

et al. 2008

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Die klassischen Verfahren der Carbonylallylierung, ‐propargylierung und ‐vinylierung setzen auf die Verwendung von vorab gebildeten Allylmetall‐, Allenylmetall‐ bzw. Vinylmetallreagentien, was die Bildung stöchiometrischer Mengen an metallischen Nebenprodukten bedingt. Durch transferhydrierende C‐C‐Kupplung gelingt es jedoch, Carbonyladditionen auch ohne stöchiometrische Organometallreagentien oder metallische Reduktionsmittel auszuführen, wobei von einem Aldehyd oder Alkohol ausgegangen wird. In diesem Kurzaufsatz geben wir einen Überblick über Transferhydrierungsmethoden für die Carbonyladdition. Es handelt sich nebenbei um die ersten katalytischen Methoden, die eine direkte C‐H‐Funktionalisierung von Alkoholen ermöglichen.

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Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric Synthesis

Cited by 415 publications

References 59 publications

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Enantiospezifische Synthese und Allylierung ausschließlich Kohlenstoff‐substituierter, α‐chiraler Allylstannane

Katalytische Carbonyladdition durch Transferhydrierung: weg von vorab gebildeten Organometallreagentien

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