Recent development of asymmetric syntheses based on the Meerwein‐Ponndorf‐Verley reduction

Nishide, Kiyohairu; Node, Manabu

doi:10.1002/chir.10142

Cited by 81 publications

(36 citation statements)

References 59 publications

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“…The development of asymmetric MPVreactions has been described [156], notably a very selective system based on Al(III)/BINOL complexes has been reported ( Figure 46). [157] In this example the ees for all products were determined although only the configuration of the 1-phenylethylamine derivative was established.…”

Section: Meerwein-ponndorf-verley (Mpv) Reductionsmentioning

confidence: 99%

Imino Transfer Hydrogenation Reductions

Wills

2016

Topics in Current Chemistry Collections

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This review contains a summary of recent developments in the transfer hydrogenation of C=N bonds, with a particularly focus on reports from within the last 10 years and asymmetric transformations. However earlier work in the area is also discussed in order to provide context for the more recent results which are described. There is strong focus on the Ru/TsDPEN class of asymmetric transfer hydrogenation reactions originally reported by Noyori et al., together with examples of their applications, particularly to medically-valuable target molecules. The recent developments in the area of highly active imine-reduction catalysts, notably those based on iridium, are also described in some detail. There is a discussion of diastereoselective reduction methods as a route to the synthesis of chiral amines using transfer hydrogenation. The recent development of methodology for positioning reduction complexes within chiral proteins, permitting the generation of asymmetric reduction products through a directed modification of the protein environment in a controlled manner, is also discussed.

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Section: Meerwein-ponndorf-verley (Mpv) Reductionsmentioning

confidence: 99%

Imino Transfer Hydrogenation Reductions

Wills

2016

Topics in Current Chemistry Collections

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“…Unfortunately the development of the reaction in an asymmetric sense has been hindered by the requirement for the use of stoichiometric quantities of metal and, therefore, of catalyst. Solutions have been found to this problem, however, and several truly catalytic methods for ketone reductions have been reported [27] . The literature on MPV -type reductions of imines is quite limited, but a very effective system based on Al(III) BINOL complexes has been reported (Scheme 11.6 ) [28] .…”

Section: Mpv Type Reductionsmentioning

confidence: 99%

Imino Reductions by Transfer Hydrogenation

Wills

2008

Modern Reduction Methods

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11 History and BackgroundIn contrast to ketones, and in particular with respect to asymmetric reductions, the reduction of compounds containing C = N bonds has remained relatively underdeveloped. Some signifi cant breakthroughs have, however, been reported in the last ten years. This chapter will review reductions through metal hydride complexes, " Meerwein -Ponndorf -Verley ( MPV ) type " reductions, and other methods including transfer hydrogenation with organocatalysts and asymmetric LeuckartWallach aminations of ketones. Although there will be discussion of mechanistic aspects, the main focus of this review will be on more recent synthetic applications. The reader ' s attention is also directed to a number of recent useful reviews of this area [1] . Mechanisms of C= N Bond Reduction by Transfer HydrogenationUsing either organic or organometallic catalysts, transfer hydrogenation of imines and other C = N bond -containing substrates, is most commonly carried out using isopropanol, formic acid or a formate salt as the hydrogen source. The most commonly, but not exclusively, used metals are ruthenium, rhodium and iridium.The mechanism of the transfer hydrogenation of imines has been the subject of some extended synthetic, computational and mechanistic studies. The tutorial review by B ä ckvall [1f] provides a very good summary of this. An excellent review by Morris [1c] also contains an incisive overview of hydrogenation and transfer hydrogenation and provides a very logical nomenclature for the possible reduction reaction pathway.The mechanisms that may be considered for imine reduction are the same as for ketone reductions and may be divided into two broad classes (Figure 11.1 ). In the fi rst of these, the MPV reduction or its reverse (Oppenauer oxidation), a metal

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“…It may be possible to replace these organometallic hydride donors with a secondary alcohol, such as 2-propanol, which acts as a hydride donor in the Meerwein-Ponndorf-Verley reduction. [17] The second limitation is the requirement for the large-scale availability of allenes. These compounds are generally prepared by multistep procedures, which again require large amounts of chemicals and energy.…”

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Synthesis of β,γ‐Unsaturated Acids from Allenes and Carbon Dioxide

North

2009

Angew Chem Int Ed

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Hidden talent: Often perceived to be too thermodynamically and kinetically inert to be a useful chemical feedstock, carbon dioxide adds to allenes under exceptionally mild reductive conditions in the presence of a palladium pincer complex to give beta,gamma-unsaturated carboxylic acids (see scheme). This transformation is discussed in the context of the requirements for CO(2) fixation. DMF = N,N-dimethylformamide, Tf = trifluoromethanesulfonyl.

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Recent development of asymmetric syntheses based on the Meerwein‐Ponndorf‐Verley reduction

Cited by 81 publications

References 59 publications

Imino Transfer Hydrogenation Reductions

Imino Transfer Hydrogenation Reductions

Imino Reductions by Transfer Hydrogenation

Synthesis of β,γ‐Unsaturated Acids from Allenes and Carbon Dioxide

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