CH Functionalization/Asymmetric Michael Addition Cascade Enabled by Relay Catalysis: Metal Carbenoid Used for CC Bond Formation

2014 ◽  
Vol 126 (40) ◽  
pp. 10939-10943 ◽  
Author(s):  
Dian-Feng Chen ◽  
Feng Zhao ◽  
Yue Hu ◽  
Liu-Zhu Gong
Keyword(s):  
Michael Addition ◽  
Bond Formation ◽  
Asymmetric Michael Addition

scholarly journals Organocatalysis for the Asymmetric Michael Addition of Cycloketones and α, β-Unsaturated Nitroalkenes

Catalysts ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 1004
Author(s):  
Jae Ho Shim ◽  
Byung Kook Ahn ◽  
Ji Yeon Lee ◽  
Hyeon Soo Kim ◽  
Deok-Chan Ha
Keyword(s):  
Nitro Group ◽  
Michael Addition ◽  
Primary Amine ◽  
Bond Formation ◽  
Hydrogen Bond Formation ◽  
Carbon Bond ◽  
Chiral Diamine ◽  
Asymmetric Michael Addition ◽  
Carbon Carbon Bond ◽  
High Level

Michael addition is one of the most important carbon–carbon bond formation reactions. In this study, an (R, R)-1,2-diphenylethylenediamine (DPEN)-based thiourea organocatalyst was applied to the asymmetric Michael addition of nitroalkenes and cycloketones to produce a chiral product. The primary amine moiety in DPEN reacts with the ketone to form an enamine and is activated through the hydrogen bond formation between the nitro group in the α, β-unsaturated nitroalkene and thiourea. Here, the aim was to obtain an asymmetric Michael product through the 1,4-addition of the enamine to an alkene to form a new carbon–carbon bond. As a result, the primary amine of the chiral diamine was converted into an enamine. The reaction proceeded with a relatively high level of enantioselectivity achieved using double activation through the hydrogen bonding of the nitro group and thiourea. Michael products with high levels of enantioselectivity (76–99% syn ee) and diastereoselectivity (syn/anti = 9/1) were obtained with yields in the range of 88–99% depending on the ketone.

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

P−C and C−C Bond Formation by Michael Addition in Platinum-Catalyzed Hydrophosphination and in the Stoichiometric Reactions of Platinum Phosphido Complexes with Activated Alkenes

2006 ◽  
Vol 25 (24) ◽  
pp. 5757-5767 ◽  
Author(s):  
Corina Scriban ◽  
David S. Glueck ◽  
Lev N. Zakharov ◽  
W. Scott Kassel ◽  
Antonio G. DiPasquale ◽  
...  
Keyword(s):  
Michael Addition ◽  
Bond Formation

ChemInform Abstract: Asymmetric Michael Addition of Ketones to Nitroolefins: Pyrrolidinyl-oxazole-carboxamides as New Efficient Organocatalysts.

ChemInform ◽  
2015 ◽  
Vol 46 (12) ◽  
pp. no-no
Author(s):  
Ahmed Kamal ◽  
Manda Sathish ◽  
Vunnam Srinivasulu ◽  
Jadala Chetna ◽  
Kunta Chandra Shekar ◽  
...  
Keyword(s):  
Michael Addition ◽  
Asymmetric Michael Addition

scholarly journals Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

2017 ◽  
Vol 13 ◽  
pp. 612-619 ◽  
Author(s):  
Alejandro Castán ◽  
Ramón Badorrey ◽  
José A Gálvez ◽  
María D Díaz-de-Villegas
Keyword(s):  
Michael Addition ◽  
Bulky Substituent ◽  
Asymmetric Michael Addition ◽  
Iodination Reaction ◽  
Chiral Imines ◽  
New Compounds ◽  
The Michael Addition

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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