The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C–N bond formation and N–O bond cleavage in one-pot for α-amination of ketones

2015 ◽  
Vol 51 (73) ◽  
pp. 13976-13979 ◽  
Author(s):  
Isai Ramakrishna ◽  
Gowri Sankar Grandhi ◽  
Harekrishna Sahoo ◽  
Mahiuddin Baidya
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Aldol Reaction ◽  
One Pot ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

A practical protocol for the α-amination of ketones (up to 99% yield) has been developed via the Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds.

Temperature-controlled Mukaiyama aldol reaction of cyclododecanone (CDD) with aromatic aldehydes promoted by TMSCl via the (TMS)3Si intermediate generated in situ

2016 ◽  
Vol 40 (4) ◽  
pp. 3833-3842 ◽  
Author(s):  
Venkatesan Sathesh ◽  
Kulathu I. Sathiyanarayanan
Keyword(s):  
Aldol Reaction ◽  
Aromatic Aldehydes ◽  
Diastereoselective Synthesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Temperature Controlled ◽  
Sterically Hindered

A temperature controlled chemo-, regio- and diastereoselective synthesis of enones and Mukaiyama aldol reaction have been developed using sterically hindered CDD with organosilane as a catalyst.

Modern Synthesis and Chemistry of Stabilized, Ketene N,O-Acetals

Synthesis ◽  
2021 ◽  
Author(s):  
Timothy J. Paris ◽  
Rachel Willand-Charnley
Keyword(s):  
Aldol Reaction ◽  
Diels Alder ◽  
First Century ◽  
Mukaiyama Aldol Reaction ◽  
Ability To Act ◽  
Mukaiyama Aldol ◽  
Recent Developments ◽  
Electron Withdrawing Group ◽  
The Stability

Ketene N,O-acetals are robust and versatile synthons. Herein, we outline the synthesis of stable ketene N,O-acetals in the twenty-first century. In addition, we review recent developments in the chemistry of ketene N,O-acetals, as it applies to the vinylogous Mukaiyama aldol reaction, electrolysis, and pericyclic transformations. While dated reports rely on in situ use, modern methods of ketene N,O-acetal synthesis are heavily oriented towards producing products with high “bench” stability; moreover, in the present century, chemists typically enhance the stability of ketene N,O-acetals by positioning an electron-withdrawing group at the β-terminus or at the N-position. As propitious substrates in the vinylogous Mukaiyama aldol reaction, ketene N,O-acetals readily provide polyketide adducts with high regioselectivity. When exposed to electrolysis conditions, the title functional group forms a reactive radical cation and cleanly couples with a variety of activated olefins. Given their electron-rich nature, ketene N,O-acetals act as facile substrates in several rearrangement reactions; further, ketene N,O-acetals reserve the ability to act as either dienophiles or dienes in Diels-Alder reactions. Lastly, ketene N,O-acetals are seemingly more stable than their O,O- counterparts and more reactive than analogous N,N- or S,S-acetals; these factors, in combination, make ketene N,O-acetals advantageous substitutes for other ketene acetal homologs.

Mukaiyama Aldol Reaction Catalyzed by (Benz)imidazolium-Based Halogen Bond Donors

2020 ◽  
Author(s):  
Revannath L. Sutar ◽  
Nikita Erochok ◽  
Stefan Huber
Keyword(s):  
Halogen Bond ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Background Reaction ◽  
Strong Performance ◽  
The Stability ◽  
Elemental Iodine

A series of cationic monodentate and bidentate iodo(benz)­imidazolium-based halogen bond (XB) donors were employed as catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant showed noticeable activity, a <i>syn</i>-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BAr<sup>F</sup><sub>4</sub> salts, PF<sub>6</sub> or OTf salts were either inactive or showed background reaction. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.

ChemInform Abstract: Mukaiyama Aldol Reaction of Trimethylsilyl Enolate with Aldehyde Catalyzed by CuI.

ChemInform ◽  
2013 ◽  
Vol 44 (22) ◽  
pp. no-no
Author(s):  
Hima Rani Kalita ◽  
Arun Jyoti Borah ◽  
Prodeep Phukan
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

ChemInform Abstract: Study of the Lanthanide-Catalyzed, Aqueous, Asymmetric Mukaiyama Aldol Reaction.

ChemInform ◽  
2012 ◽  
Vol 43 (43) ◽  
pp. no-no
Author(s):  
Yujiang Mei ◽  
Derek J. Averill ◽  
Matthew J. Allen
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes

2014 ◽  
Vol 43 (1) ◽  
pp. 2-10 ◽  
Author(s):  
Gheorghe-Doru Roiban ◽  
Adriana Ilie ◽  
Manfred T. Reetz
Keyword(s):  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol
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