ChemInform Abstract: Thionium Ion Promoted Michael Acceptor: A Sequence of Pummerer/Michael Reactions for the Stereoselective Synthesis of 5-(1-(Arylthio)vinyl)-oxazolines.

ChemInform ◽  
2014 ◽  
Vol 45 (28) ◽  
pp. no-no
Author(s):  
Shimin Xu ◽  
Qianyun Zhang ◽  
Hongwei Zhou
Keyword(s):  
Stereoselective Synthesis ◽  
Michael Reactions ◽  
Michael Acceptor

ChemInform Abstract: Organocatalytic Domino Mannich Aza-Michael Reactions Towards the Stereoselective Synthesis of Highly Substituted Pipecolic Esters.

ChemInform ◽  
2009 ◽  
Vol 40 (8) ◽  
Author(s):  
Souad Khaliel ◽  
Mecheril Valsan Nandakumar ◽  
Harald Krautscheid ◽  
Christoph Schneider
Keyword(s):  
Stereoselective Synthesis ◽  
Michael Reactions

ChemInform Abstract: Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives.

ChemInform ◽  
2011 ◽  
Vol 42 (22) ◽  
pp. no-no
Author(s):  
Peng He ◽  
Xiaohua Liu ◽  
Jian Shi ◽  
Lili Lin ◽  
Xiaoming Feng
Keyword(s):  
Stereoselective Synthesis ◽  
Michael Reactions

Organocatalytic Sequential Michael Reactions: Stereoselective Synthesis of Multifunctionalized Tetrahydroindan Derivatives

2011 ◽  
Vol 13 (5) ◽  
pp. 936-939 ◽  
Author(s):  
Peng He ◽  
Xiaohua Liu ◽  
Jian Shi ◽  
Lili Lin ◽  
Xiaoming Feng
Keyword(s):  
Stereoselective Synthesis ◽  
Michael Reactions

scholarly journals Electron Rich Triarylphosphines as Nucleophilic Catalysts for Oxa-Michael Reactions

2021 ◽  
Author(s):  
Susanne Fischer ◽  
Simon Renner ◽  
Adrian Daniel Böse ◽  
Christian Slugovc
Keyword(s):  
Room Temperature ◽  
Oxidation Stability ◽  
Strong Impact ◽  
Michael Adduct ◽  
Michael Additions ◽  
Michael Reactions ◽  
Repeat Units ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Reaction Speed

Herein, we study the activity of methoxysubstituted arylphosphines (4-methoxy-phenyl)diphenylphosphine (MMTPP) and tris(4-trimethoxyphenyl)phosphine (TMTPP) in catalyzing oxa-Michael additions in comparison to commonly used triphenylphosphine (TPP). Acrylonitrile, acryl amide and divinyl sulfone are used as Michael acceptors and propargyl alcohol, allyl alcohol, n-propanol and i-propanol are assessed as Michael donors. In many cases, catalyst loadings of only 1 mol% in respect to the Michael acceptor are sufficient to provide full conversion towards the Michael adduct in 24 h at room temperature. Generally, TMTPP is the most active catalyst in all cases. The experimental activity trend was rationalized by calculating the Michael acceptor affinities of all phosphine – Michael acceptor combinations. Besides this parameter, the acidity of the alcohol has a strong impact on the reaction speed. The oxidation stability of the phosphines was evaluated and electron richest TMTPP was found to be only slightly more sensitive to oxidation than TPP. Finally, the catalysts were employed in the oxa-Michael polymerization of 2-hydroxyethyl acrylate. With TMTPP polymers characterized by number average molar masses of about 1200 g/mol at room temperature are accessible. Polymerizations carried out at 80 °C resulted in macromolecules containing a considerable share of Rauhut-Currier type repeat units and consequently lower molar masses were obtained.

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