ChemInform Abstract: The Michael Addition of Dimethyl Malonate to α,β- Unsaturated Aldehydes Catalyzed by Proline Lithium Salt.

ChemInform ◽  
2010 ◽  
Vol 23 (11) ◽  
pp. no-no
Author(s):  
M. YAMAGUCHI ◽  
N. YOKOTA ◽  
T. MINAMI
1994 ◽  
Vol 59 (12) ◽  
pp. 2621-2631 ◽  
Author(s):  
Ľubomír Šebo ◽  
Ján Šraga ◽  
Grety Rihs ◽  
Štefan Toma

The stereoselectivity of the Michael addition of several C-nucleophiles to 3-phenyl-1-(η6-o-tolyltricarbonylchromium)propenone has been studied. The ratio of diastereoisomers formed varied from 65 : 35 (malonodinitrile), 72 : 28 (methyl cyanoacetate) and 78 : 22 (nitromethane) and to 90 : 10 (dimethyl malonate). The ratio of diastereoisomers 63 : 37 was found even when addition of dimethyl malonate was carried out at 75 °C in methanol using piperidine as the catalyst. The (S,R) or (R,S) configuration of the main pair of isomers was proved by the X-ray analysis of the dimethyl malonate adduct.


Synthesis ◽  
1979 ◽  
Vol 1979 (02) ◽  
pp. 107-109 ◽  
Author(s):  
G. V. Kryshtal ◽  
V. V. Kulganek ◽  
V. F. Kucherov ◽  
L. A. Yanovskaya

2005 ◽  
pp. 669-671 ◽  
Author(s):  
N. Srilakshmi Krishnaveni ◽  
K. Surendra ◽  
K. Rama Rao

2014 ◽  
Vol 2014 ◽  
pp. 1-15 ◽  
Author(s):  
Abdullah M. A. Al Majid ◽  
Mohammad Shahidul Islam ◽  
Assem Barakat ◽  
Mohamed H. M. Al-Agamy ◽  
Mu. Naushad

The importance of cooperative hydrogen-bonding effects has been demonstrated using novel 3-methylenecyclopropane-1,2-dicarboxylic acid (Feist’s acid (FA)) as hydrogen bond donor catalysts for the addition of indole and pyrrole totrans-β-nitrostyrene derivatives. Because of the hydrogen bond donor (HBD) ability, Feist’s acid (FA) has been introduced as a new class of hydrogen bond donor catalysts for the activation of nitroolefin towards nucleophilic substitution reaction. It has effectively catalyzed the Michael addition of indoles and pyrrole toβ-nitroolefins under optimum reaction condition to furnish the corresponding Michael adducts in good to excellent yields (up to 98%). The method is general, atom-economical, convenient, and eco-friendly and could provide excellent yields and regioselectivities. Some newly synthesized compounds were for examinedin vitroantimicrobial activity and their preliminary results are reported.


2017 ◽  
Vol 13 ◽  
pp. 612-619 ◽  
Author(s):  
Alejandro Castán ◽  
Ramón Badorrey ◽  
José A Gálvez ◽  
María D Díaz-de-Villegas

New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.


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