Transfer Hydrogenation in Water: Enantioselective, Catalytic Reduction of (<i>E</i>)-β,β-Disubstituted Nitroalkenes

Soltani, Omid; Ariger, Martin A.; Carreira, Erick M.

doi:10.1021/ol901332e

Cited by 90 publications

(18 citation statements)

References 40 publications

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“…In 2009, Carreira and co‐workers presented an enantioselective transfer hydrogenation of ( E )‐β,β‐disubstituted nitroalkenes in water using Ir complex 159 as catalyst (Scheme ) 95. A series of nitroalkenes were efficiently hydrogenated under mild and easily handled conditions, giving chiral nitroalkanes with excellent enantioselectivities in high yields.…”

Section: Mnh Catalysismentioning

confidence: 99%

The NH Functional Group in Organometallic Catalysis

2013

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The organometallic approach is one of the most active topics in catalysis. The application of NH functionality in organometallic catalysis has become an important and attractive concept in catalyst design. NH moieties in the modifiers of organometallic catalysts have been shown to have various beneficial functions in catalysis by molecular recognition through hydrogen bonding to give catalyst-substrate, ligand-ligand, ligand-catalyst, and catalyst-catalyst interactions. This Review summarizes recent progress in the development of the organometallic catalysts based on the concept of cooperative catalysis by focusing on the NH moiety.

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Section: Mnh Catalysismentioning

confidence: 99%

The NH Functional Group in Organometallic Catalysis

2013

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“…In spite of the success of asymmetric iridium catalysts for the direct hydrogenation of alkenes, there has been very limited research into the use of alternative hydrogen donors. Carreira and coworkers have reported an enantioselective reduction of nitroalkenes in water using formic acid and the iridium aqua complex 69 [66]. For example, the reduction of nitroalkene 70 led to the formation of the product 71 in good yield and enantioselectivity (Scheme 17).…”

Section: Asymmetric Transfer Hydrogenation Of Other Substratesmentioning

confidence: 99%

Iridium-Catalyzed Hydrogen Transfer Reactions

Saidi

Williams

2010

Iridium Catalysis

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This chapter describes the application of iridium complexes to catalytic hydrogen transfer reactions. Transfer hydrogenation reactions provide an alternative to direct hydrogenation for the reduction of a range of substrates. A hydrogen donor, typically an alcohol or formic acid, can be used as the source of hydrogen for the reduction of carbonyl compounds, imines, and alkenes. Heteroaromatic compounds and even carbon dioxide have also been reduced by transfer hydrogenation reactions. In the reverse process, the oxidation of alcohols to carbonyl compounds can be achieved by iridium-catalyzed hydrogen transfer reactions, where a ketone or alkene is used as a suitable hydrogen acceptor. The reversible nature of many hydrogen transfer processes has been exploited for the racemization of alcohols, where temporary removal of hydrogen generates an achiral ketone intermediate. In addition, there is a growing body of work where temporary removal of hydrogen provides an opportunity for using alcohols as alkylating agents. In this chemistry, an iridium catalyst "borrows" hydrogen from an alcohol to give an aldehyde or ketone intermediate, which can be transformed into either an imine or alkene under the reaction conditions. Return of the hydrogen from the catalyst provides methodology for the formation of amines or C-C bonds where the only by-product is typically water.

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“…Chiral vicinal diamines have been employed in the development of transition metal based catalysts [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16], organocatalysts [17][18][19][20] and pharmaceuticals [21]. Chiral derivatizing agents (CDA) continue to be an important and convenient tool for determining the enantiopurity of chiral compounds.…”

Section: Introductionmentioning

confidence: 99%