A New Class of Chiral Pyrrolidine−Pyridine Conjugate Base Catalysts for Use in Asymmetric Michael Addition Reactions

2004 ◽  
Vol 126 (31) ◽  
pp. 9558-9559 ◽  
Author(s):  
Takaaki Ishii ◽  
Shingo Fujioka ◽  
Yusuke Sekiguchi ◽  
Hiyoshizo Kotsuki
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
Base Catalysts ◽  
New Class ◽  
Asymmetric Michael Addition ◽  
Conjugate Base

A new class of chiral pyrrolidine for asymmetric Michael addition reactions. New mechanism via simple 4+2 type attack of the enamine on the trans-nitrostyrene

Tetrahedron ◽  
2007 ◽  
Vol 63 (3) ◽  
pp. 740-747 ◽  
Author(s):  
David Diez ◽  
M. Jose Gil ◽  
Rosalina F. Moro ◽  
Isidro S. Marcos ◽  
P. García ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
New Class ◽  
Asymmetric Michael Addition

scholarly journals Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1159
Author(s):  
Eskedar Tessema ◽  
Vijayanath Elakkat ◽  
Chiao-Fan Chiu ◽  
Jing-Hung Zheng ◽  
Ka Long Chan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Polar Solvent ◽  
Addition Reaction ◽  
High Yield ◽  
Addition Reactions ◽  
Polar Solvents ◽  
Unsaturated Bond ◽  
Base Catalysts ◽  
Michael Additions

Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP·Hsac) salt and a fluorous long-chained pyridine (4-Rf-CH2OCH2-py, where Rf = C11F23). These catalysts have been synthesized and characterized by Lu’s group. The phospha-Michael addition of diisopropyl, dimethyl or triethyl phosphites to α, β-unsaturated malonates in the presence of those catalysts showed very good reactivity with high yield at 80–100 °C in 1–4.5 h with high catalytic recovery and reusability. With regard to significant catalytic recovery, sometimes more than eight cycles were observed for DMAP·Hsac adduct by using non-polar solvents (e.g., ether) to precipitate out the catalyst. In the case of the fluorous long-chained pyridine, the thermomorphic method was used to efficiently recover the catalyst for eight cycles in all the reactions. Thus, the easy separation of the catalysts from the products revealed the outstanding efficacy of our systems. To our knowledge, these are good examples of the application of recoverable organo-catalysts to the DMAP·Hsac adduct by using non-polar solvent and a fluorous long-chained pyridine under the thermomorphic mode in phospha-Michael addition reactions.

Pyrrolidinyl-Camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to β-Nitroalkenes

2010 ◽  
Vol 16 (23) ◽  
pp. 7030-7038 ◽  
Author(s):  
Ying-Fang Ting ◽  
Chihliang Chang ◽  
Raju Jannapu Reddy ◽  
Dhananjay R. Magar ◽  
Kwunmin Chen
Keyword(s):  
Michael Addition ◽  
New Class ◽  
Asymmetric Michael Addition ◽  
Aldehydes And Ketones ◽  
Camphor Derivatives

scholarly journals 3,3′-Bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition.

ChemInform ◽  
2006 ◽  
Vol 37 (43) ◽  
Author(s):  
Sarah Mosse ◽  
Marju Laars ◽  
Kadri Kriis ◽  
Tonis Kanger ◽  
Alexandre Alexakis
Keyword(s):  
Michael Addition ◽  
New Class ◽  
Asymmetric Michael Addition
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