Efficient and Highly Enantioselective Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Surfactant-type Organocatalyst in the Presence of Water

Hu, Feng; Guo, Chang-Shan; Xie, Jin; Hai-liang, Zhu; Huang, Zhu

doi:10.1246/cl.2010.412

Cited by 15 publications

(1 citation statement)

References 25 publications

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“…Considerable research efforts into the development of water‐compatible organocatalysts for performing organic transformations in aqueous media have been actively pursued 4. However, only limited success has so far been achieved in Michael additions of isobutyraldehyde to nitroalkenes in aqueous systems 2b,2d,2f,2i. Furthermore, to the best of our knowledge, no such organocatalyst possessing the unique feature of promoting these reactions both in water and in organic solvents had been reported.…”

Section: Introductionmentioning

confidence: 96%

Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine‐Thioureas in Organic or Aqueous Medium

Liu

Zhang

et al. 2011

Eur J Org Chem

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Section: Introductionmentioning

confidence: 96%

Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine‐Thioureas in Organic or Aqueous Medium

Liu

Zhang

et al. 2011

Eur J Org Chem

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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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Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Free Radical Alkylation Direct Alkylation or Acylation / Organocatalysis Direct Enol or Enolate Alkylation and Acylation Enol Ethers Enol Esters Enol Boranes Enol Alanes Enol Gallium Compounds Enol Silanes Enol Stannanes and Related Compounds Enol Phosphorus Compounds Enol Triflates Enamines Nitroalkenes Imines Hydrazones Oxime Ethers Oximes Blocking Groups Alkylation and Acylation of Carbonyl Dianions Alkylation and Acylation of β‐Ketoaldehydes Alkylation and Acylation of β ‐Diketones Alkylation and Acylation of β‐Polyketones Synthesis of β‐Keto Acids, Esters, Amides, Imides, and Nitriles and Decarboxylation Alkylation and Acylation of Enones

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Efficient and Highly Enantioselective Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Surfactant-type Organocatalyst in the Presence of Water

Cited by 15 publications

References 25 publications

Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine‐Thioureas in Organic or Aqueous Medium

Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine‐Thioureas in Organic or Aqueous Medium

The Catalytic, Enantioselective Michael Reaction

Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives

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