Solvent-Free Enantioselective Michael Reactions Catalyzed by a Calixarene-Based Primary Amine Thiourea

2018 ◽  
Vol 83 (17) ◽  
pp. 10318-10325 ◽  
Author(s):  
Nicola Alessandro De Simone ◽  
Sara Meninno ◽  
Carmen Talotta ◽  
Carmine Gaeta ◽  
Placido Neri ◽  
...  
Keyword(s):  
Primary Amine ◽  
Solvent Free ◽  
Michael Reactions

Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten

2018 ◽  
Vol 73 (1) ◽  
pp. 43-74 ◽  
Author(s):  
Cindy Döring ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bonds ◽  
Structure Analysis ◽  
Secondary Amine ◽  
Primary Amine ◽  
Solvent Free ◽  
Secondary Amines ◽  
Primary Amines ◽  
Direct Reaction ◽  
X Ray

AbstractThe reaction of (tht)AuX (X=Cl or Br; tht=tetrahydrothiophene) with various primary amines L leads to products of the form [L2Au]+X−. Packing diagrams of the corresponding structures are dominated by N–H···X hydrogen bonds and (in some cases) aurophilic contacts. The cyclohexylamine derivative was already known as its dichloromethane ⅔-solvate; we have isolated the solvent-free compound and its pentane ¼-solvate, which all show different packing patterns. With acyclic secondary amines, the products are more varied; LAuX and [L2Au]+[AuX2]− were also found. These gold(I) products were generally formed in satisfactory quantities. The attempted oxidation to Au(III) derivatives with PhICl2 or Br2 proved impossible for the primary amine derivatives [although isopropylamine-trichloridogold(III) was obtained unexpectedly from the corresponding cyanide] and unsatisfactory for the secondary amine derivatives. Products LAuX3 and [L2AuX2]+[AuX4]− were identified but were formed in disappointing yields. In isolated cases protonated products (LH)+[AuCl4]−, (LH+)3[AuCl4]−(Cl−)2 or [(Et2N)2CH]+[AuBr4]− were formed, presumably by involvement of the dichloromethane solvent and/or adventitious water. Here also the yields were poor, and some products arose as mixtures. Direct reaction of amines with AuCl3 or (tht)AuX3 was also unsuccessful. All products were characterized by X-ray structure analysis.

Chiral primary amine thiourea promoted highly enantioselective Michael reactions of isobutylaldehyde with maleimides

Tetrahedron ◽  
2010 ◽  
Vol 66 (46) ◽  
pp. 8928-8932 ◽  
Author(s):  
Jian-Fei Bai ◽  
Lin Peng ◽  
Liang-liang Wang ◽  
Li-Xin Wang ◽  
Xiao-Ying Xu
Keyword(s):  
Primary Amine ◽  
Michael Reactions

Histamine, an effective initiator for the synthesis of polysulfides

2020 ◽  
Vol 5 (2) ◽  
pp. 258-262
Author(s):  
Alejandro Cabrera-García ◽  
Rubén Blay-Roger ◽  
Vincent Blay ◽  
Ángel G. Ravelo ◽  
Pedro Martín-Zarza
Keyword(s):  
Primary Amine ◽  
Solvent Free ◽  
Metal Free

A solvent-free and metal-free synthesis of highly pure polysulfides is described using histamine, a primary amine, as an initiator.

ChemInform Abstract: Chiral Primary Amine Thiourea Promoted Highly Enantioselective Michael Reactions of Isobutyraldehyde with Maleimides.

ChemInform ◽  
2011 ◽  
Vol 42 (11) ◽  
pp. no-no
Author(s):  
Jian-Fei Bai ◽  
Lin Peng ◽  
Liang-liang Wang ◽  
Li-Xin Wang ◽  
Xiao-Ying Xu
Keyword(s):  
Primary Amine ◽  
Michael Reactions

Chiral Primary Amine Tagged to Ionic Group as Reusable Organocatalyst for Asymmetric Michael Reactions of C-Nucleophiles with α,β-Unsaturated Ketones

2012 ◽  
Vol 354 (16) ◽  
pp. 3078-3086 ◽  
Author(s):  
Alexander S. Kucherenko ◽  
Dmitry E. Siyutkin ◽  
Albert G. Nigmatov ◽  
Alexander O. Chizhov ◽  
Sergei G. Zlotin
Keyword(s):  
Primary Amine ◽  
Unsaturated Ketones ◽  
Ionic Group ◽  
Michael Reactions
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