Enantiomerically Enriched Allylic Alcohols and Allylic Amines via C–C Bond-Forming Hydrogenation: Asymmetric Carbonyl and Imine Vinylation

Skucas, Eduardas; Ngai, Ming‐Yu; Komanduri, Venukrishnan; Krische, Michael J.

doi:10.1021/ar7001123

Cited by 275 publications

(86 citation statements)

References 145 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[1–3] Among nitrogen-containing molecules, aminomethylated arenes are privileged substructures that are found in many bioactive materials, exhibiting activity against a wide array of diseases. [4–7] …”

mentioning

confidence: 99%

α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

2015

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

2015

View full text Add to dashboard Cite

show abstract

“…In conventional synthetic routes, it is not unusual to rely on a sequence of three stoichiometric organometallic reagents (some having pyrophoric properties) to achieve a single transformation, but Krische's catalytic method eliminates stoichiometric byproducts, incorporating all the atoms of the reactants into the final product (19) (Figure 3).…”

Section: Catalysismentioning

confidence: 99%

Green chemistry: the emergence of a transformative framework

Anastas

Beach

2007

Green Chemistry Letters and Reviews

View full text Add to dashboard Cite

Since the Twelve Principles of Green Chemistry were formulated in the 1990s, there have been tremendous successes in developing new products and processes to be more compatible with human health, the environment, and sustainability goals. This review gives a sampling of research successes from the last 20 years, including advances in synthetic efficiency, application of alternative synthetic methods, use of less hazardous solvents and reagents, and development of renewable resources for chemical feedstocks. The future of green chemistry will depend on innovations that consolidate and integrate these achievements that have been made, using all Twelve Principles as a framework for intentional design. Designing for sustainability and reduced hazard should not be viewed as constraining, but rather as providing the freedom to explore and invent, bridging continents and scientific disciplines to create new solutions.

show abstract

“…In addition to the nickelcatalyzed variants that are the subject of this chapter, important advances have been made with titanium - [9 -13] , iridium - [14] , and rhodium -catalyzed variants [15] . Many reducing agents have been employed, and the most widely used classes include silanes, organozincs, organoboranes, molecular hydrogen, and alcohols.…”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Reductive Couplings and Cyclizations

Malik

Baxter

Montgomery

2010

Catalysis Without Precious Metals

View full text Add to dashboard Cite

Many classes of standard organic transformations involve the coupling or cycloaddition of two different π -components to assemble a more functionalized product. Many such processes are amenable to the union of two complex fragments, thus allowing convergent approaches to complex organic molecules. Diels -Alder cycloadditions, Prins addition reactions, and ene reactions are examples of broadly useful processes that involve the union of two π -components in a selective manner. As a complement to these classical transformations, the reductive coupling of two π -components provides an alternative strategy for assembly of complex fragments from the same types of starting materials [1 -8] . Whereas the starting components resemble those required for the types of standard organic transformations noted above, the products obtained differ structurally and are obtained in a reduced oxidation state based on the action of the reducing agent employed.A number of transition metal catalyst/reducing agent combinations are known to promote various reductive coupling processes. In addition to the nickelcatalyzed variants that are the subject of this chapter, important advances have been made with titanium -[9 -13] , iridium - [14] , and rhodium -catalyzed variants [15] . Many reducing agents have been employed, and the most widely used classes include silanes, organozincs, organoboranes, molecular hydrogen, and alcohols. The specifi c focus of this chapter will be the development of nickel -catalyzed reductive couplings and cyclizations between a polar π -component and a non -polar π -component. This strategy allows the two π -components to be differentiated in catalytic reactions, and thus avoids homocoupling processes that are often problematic in transformations of this type. The use of either aldehydes or α , β -unsaturated carbonyls as the polar component, and alkynes as the non -polar component has been a primary focus of our laboratories and will be the subject of this chapter. Extensive related developments involving dienes as the non -polar component reported by the laboratories of Mori [16] , Sato [17] , and Tamaru [18] have been reviewed elsewhere [3] and will not be extensively discussed in this 8 Catalysis Without Precious Metals. Edited by R. Morris Bullock

show abstract

Enantiomerically Enriched Allylic Alcohols and Allylic Amines via C–C Bond-Forming Hydrogenation: Asymmetric Carbonyl and Imine Vinylation

Cited by 275 publications

References 145 publications

α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

Green chemistry: the emergence of a transformative framework

Nickel‐Catalyzed Reductive Couplings and Cyclizations

Contact Info

Product

Resources

About