Chiral Ionic Liquids Bearing O‐Silylated α,α‐Diphenyl (S)‐ or (R)‐Prolinol Units: Recoverable Organocatalysts for Asymmetric Michael Addition of Nitroalkanes to α,β‐Enals

Maltsev, Oleg V.; Kucherenko, Alexander S.; Beletskaya, I. P.; Tartakovsky, Vladimir A.; Zlotin, Sergei G.

doi:10.1002/ejoc.201000239

Cited by 70 publications

(37 citation statements)

References 88 publications

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“…The enantioselectivity was determined by HPLC analysis (77% ee, Daicel CHIRALPAK AD-H, 5% isopropanol/hexane, 1.0 mL/min, 229 nm; t r (major enantiomer) = 18. Spectroscopic data of γ-nitroketones 4 are in agreement with published data [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32]. …”

Section: Typical Procedures For the Michael Addition Of Nitroalkanes Tsupporting

confidence: 84%

“…As pioneering works in organocatalytic asymmetric Michael addition of carbon nucleophiles to α,β-unsaturated carbonyl compounds, Yamaguchi's group reported that Michael addition of malonates to enones could be catalyzed by a proline alkali metal salt [6][7][8][9][10][11][12]. They later succeeded in the asymmetric Michael addition of nitroalkanes to enones using a proline rubidium salt-catalyst [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32]. We recently reported that an O-silylated L-serine lithium salt was an effective catalyst for asymmetric Michael addition of malonates to enones to give various 1,5-ketoesters in good yields with high enantioselectivity [33].…”

Section: Introductionmentioning

confidence: 99%

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Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones

et al. 2011

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Section: Typical Procedures For the Michael Addition Of Nitroalkanes Tsupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones

et al. 2011

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“…Ionic liquids (IL) have shown interesting ability as phase tags for organocatalysts. [6][7][8][9][10][11][12][13][14][15] Ionic liquid tagged catalysts can be tuned to attain a required physical property, such as solubility, or compatibility with the reaction medium and thermal stability. 16 In this way improved recovery and recycling and sometimes even better catalytic activity can be attained.…”

Section: Introductionmentioning

confidence: 99%

“…16 In this way improved recovery and recycling and sometimes even better catalytic activity can be attained. [17][18][19]14 Accordingly, we envisaged that a properly functionalized ionic liquid tag can render TADDOLs novel properties and improve their usefulness as organocatalysts. Immobilizing TADDOL catalysts with ionic liquids has the potential to render the TADDOLs tuneable solubility for working under homogeneous conditions, without diminishing their catalytic activity or their amount of catalyst loading, unlike TADDOLs immobilized on solid supports.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and application of azolium ionic liquid tagged TADDOL catalysts

Yacob¹,

Liebscher²

2012

Arkivoc

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Ionic liquid (IL) tagged organocatalysts based on TADDOL (α,α,α',α'-tetraaryl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol) comprising various aryl substituents tethered with triazolium and imidazolium based ionic liquids are synthesised in good yields. Investigation of these IL-tagged catalysts on hydrogen-bonding catalyzed hetero-Diels-Alder (HDA) reactions between activated dienes (such as Rawal's diene and Brassard's diene) and benzaldehyde indicated their potential and limitations for applications in organocatalysis.

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The Catalytic, Enantioselective Michael Reaction

et al. 2016

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The catalytic enantioselective Michael reaction is the conjugate addition of a resonance‐stabilized carbanion to an electron‐poor olefin (an αβ‐unsaturated carbonyl compound or a related derivative) mediated by substoichiometric amounts of a chiral catalyst that enables stereocontrol in the newly generated stereocenter(s). This reaction allows the direct enantioselective construction of substituted 1,5‐dicarbonyl compounds or related architectures through the appropriate selection of the enolizable carbonyl compound employed as pronucleophile and the Michael acceptor. A variety of catalyst architectures have been described that make it possible to carry out this reaction with superior levels of chemical efficiency and high enantio‐ and stereocontrol, and also under conditions that tolerate a wide variety of functional groups. Both transition metal catalysis and organocatalysis have been employed as methodological approaches for carrying out this reaction in an enantioselective manner. This chapter describes different catalytic systems and methods developed for achieving enantioselective Michael reactions through the end of 2012, including a detailed mechanistic explanation of the different generic modes of substrate activation operating with each type of catalyst and their associated stereochemical aspects. The intention is to provide researchers interested in applying this methodology to their own synthetic strategies with a suitable starting point for identifying an efficient synthetic approach. In addition, the preparation of selected catalysts that are excellent for a particular pairing of substrates in this reaction, together with practical experimental protocols are described and some examples in which these methodologies have been applied to total synthesis have been included. This chapter is limited exclusively to those examples in which the final Michael addition product is obtained after protonation of the conjugate addition intermediate and therefore, tandem, domino, or cascade processes initiated by Michael reactions lie outside the scope of this work. Supplemental references are provided for articles published after the 2012 cut‐off date through the first half of 2015.

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Chiral Ionic Liquids Bearing O‐Silylated α,α‐Diphenyl (S)‐ or (R)‐Prolinol Units: Recoverable Organocatalysts for Asymmetric Michael Addition of Nitroalkanes to α,β‐Enals

Cited by 70 publications

References 88 publications

Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones

Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones

Synthesis and application of azolium ionic liquid tagged TADDOL catalysts

The Catalytic, Enantioselective Michael Reaction

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