ChemInform Abstract: High Pressure Organic Chemistry. Part 40. Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers Through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure.

ChemInform ◽  
2015 ◽  
Vol 46 (46) ◽  
pp. no-no
Author(s):  
Ryo Horinouchi ◽  
Kouhei Kamei ◽  
Riki Watanabe ◽  
Nobushige Hieda ◽  
Naoki Tatsumi ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
High Pressure ◽  
Michael Addition ◽  
Primary Amine ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Quaternary Carbon ◽  
Michael Addition Reaction ◽  
Cyclic Ketones ◽  
Stereogenic Centers

Efficient Organocatalytic Michael Addition Reaction of β−Ketoesters under High Pressure

Heterocycles ◽  
2013 ◽  
Vol 87 (11) ◽  
pp. 2351 ◽  
Author(s):  
Hiyoshizo Kotsuki ◽  
Maya Moritaka ◽  
Keiji Nakano
Keyword(s):  
High Pressure ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

scholarly journals Michael Addition of Imidazole to α, β -Unsaturated Carbonyl/Cyano Compound

2018 ◽  
Vol 5 (1) ◽  
pp. 18-31
Author(s):  
Seetaram Mohapatra ◽  
Nilofar Baral ◽  
Nilima Priyadarsini Mishra ◽  
Pravati Panda ◽  
Sabita Nayak
Keyword(s):  
Organic Chemistry ◽  
Amino Acids ◽  
Anticancer Agents ◽  
Michael Addition ◽  
Addition Reaction ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Michael Addition Reaction ◽  
Cyano Compounds ◽  
Nitrogen Bond

Introduction: Aza-Michael addition is an important reaction for carbon-nitrogen bond formation in synthetic organic chemistry. Expalantion: Conjugate addition of imidazole to α,β-unsaturated carbonyl/cyano compounds provides significant numbers of the biologically and synthetically interesting products, such as β-amino acids and β-lactams, which have attracted great attention for their use as key intermediates of anticancer agents, antibiotics and other drugs. Conclusion: This review addresses most significant method for the synthesis of N-substituted imidazole derivatives following Michael addition reaction of imidazole to α,β-unsaturated carbonyl/cyano compounds using ionic liquid/base/acid/enzyme as catalysts from year 2007-2017.

A short enantioselective synthesis of 3-epi-jaspine B and (+)-oxybiotin via an intramolecular tandem desilylation oxa-Michael addition strategy

RSC Advances ◽  
2014 ◽  
Vol 4 (91) ◽  
pp. 49770-49774 ◽  
Author(s):  
Anil M. Shelke ◽  
Varun Rawat ◽  
Arumugam Sudalai ◽  
Gurunath Suryavanshi
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Asymmetric Epoxidation ◽  
Michael Addition Reaction ◽  
New Synthesis ◽  
Sharpless Asymmetric Epoxidation ◽  
Jaspine B

A new synthesis of cytotoxic 3-epi-jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee) is described starting from cis-2-butene-1,4-diol. The key reactions employed in the synthesis are Sharpless asymmetric epoxidation and a novel tandem desilylation-oxa Michael addition reaction.

Enantioselective Synthesis of β-Nitro Phosphonates Catalyzed by a Secondary Amine Bisthiourea

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1385-1389 ◽  
Author(s):  
Noor-ul Khan ◽  
Mohd Nazish ◽  
Ajay Jakhar ◽  
Naveen Gupta ◽  
Rukhsana Kureshy
Keyword(s):  
Spectroscopic Study ◽  
Secondary Amine ◽  
Michael Addition ◽  
Molecular Sieves ◽  
Addition Reaction ◽  
Probable Mechanism ◽  
Enantioselective Synthesis ◽  
Michael Addition Reaction

An enantioselective Michael addition of diphenyl phosphonate to nitroalkenes has been developed by using a secondary amine bisthiourea catalyst to access enantiomerically enriched β-nitro phosphonates. In this reaction, molecular sieves play a key role in achieving high and reproducible yields with a high enantioselectivities of up to 99% at –10 °C. A probable mechanism for the enantioselective Michael addition reaction was established by means of an NMR spectroscopic study.

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