Asymmetric Michael Addition of α-Hydroxyketones to Nitroolefins Catalyzed by Chiral Diamine

2003 ◽  
Vol 5 (14) ◽  
pp. 2559-2561 ◽  
Author(s):  
Olivier Andrey ◽  
Alexandre Alexakis ◽  
Gérald Bernardinelli
Keyword(s):  
Michael Addition ◽  
Chiral Diamine ◽  
Asymmetric Michael Addition

Diastereodivergent Catalytic Asymmetric Michael Addition of 2-Oxindoles to α,β-Unsaturated Ketones by Chiral Diamine Catalysts

2015 ◽  
Vol 17 (11) ◽  
pp. 2732-2735 ◽  
Author(s):  
Yuan Wei ◽  
Shigang Wen ◽  
Zunwu Liu ◽  
Xinxin Wu ◽  
Bubing Zeng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Unsaturated Ketones ◽  
Chiral Diamine ◽  
Asymmetric Michael Addition ◽  
Catalytic Asymmetric

Dual Catalyst Control in the Chiral Diamine-Dipeptide-Catalyzed Asymmetric Michael Addition

Synlett ◽  
2004 ◽  
Vol 2004 (14) ◽  
pp. 2624-2626 ◽  
Author(s):  
Svetlana Tsogoeva ◽  
Sunil Jagtap
Keyword(s):  
Michael Addition ◽  
Chiral Diamine ◽  
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.

scholarly journals Asymmetric Michael Addition of α-Hydroxyketones to Nitroolefins Catalyzed by Chiral Diamine.

ChemInform ◽  
2003 ◽  
Vol 34 (44) ◽  
Author(s):  
Olivier Andrey ◽  
Alexandre Alexakis ◽  
Gerald Bernardinelli
Keyword(s):  
Michael Addition ◽  
Chiral Diamine ◽  
Asymmetric Michael Addition

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

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
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