Enzymatic Elimination from a Substituted Four-Carbon Amino Acid Coupled to Michael Addition of a β-Carbon to an Electrophilic Double Bond. Structure of the Reaction Product*

Biochemistry ◽  
1966 ◽  
Vol 5 (4) ◽  
pp. 1340-1350 ◽  
Author(s):  
Martin Flavin ◽  
Clarence Slaughter
Keyword(s):  
Amino Acid ◽  
Double Bond ◽  
Michael Addition

Recent Synthetic Approaches and Biological Evaluations of Amino Hexahydroquinolines and Their Spirocyclic Structures

2019 ◽  
Vol 19 (7) ◽  
pp. 875-915 ◽  
Author(s):  
Amr M. Abdelmoniem ◽  
Magda F. Mohamed ◽  
Doaa M. Abdelmoniem ◽  
Said A.S. Ghozlan ◽  
Ismail A. Abdelhamid
Keyword(s):  
Double Bond ◽  
Calcium Channel ◽  
Michael Addition ◽  
Antitubercular Agents ◽  
Sar Studies ◽  
Two Component ◽  
Synthetic Routes ◽  
Synthetic Approaches ◽  
Three Components

In this review, the recent synthetic approaches of amino hexahydroquinolines and their spirocyclic structures were highlighted. The synthetic routes include, two-components, three-components or fourcomponents reactions. The two-component [3+3] atom combination reaction represents the simplest method. It involves Michael addition of the electron rich β-carbon of β-enaminones to the activated double bond of cinnamonitriles followed by cyclization to yield hexahydroquinoline compounds. The bioactivity profiles and SAR studies of these compounds were also reviewed with emphasis to the utility of these substances as antimicrobial, anticancer and antitubercular agents, as well as calcium channel modulators.

Highly Stereoselective Michael Addition Reactions of CamTHP*-Desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives

2004 ◽  
Vol 6 (24) ◽  
pp. 4427-4429 ◽  
Author(s):  
Darren J. Dixon ◽  
Richard A. J. Horan ◽  
Nathaniel J. T. Monck ◽  
Paul Berg
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Amino Acid Derivatives ◽  
Addition Reactions

Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization

2016 ◽  
Vol 22 (46) ◽  
pp. 16429-16432 ◽  
Author(s):  
Yuki Kaji ◽  
Naohiro Uemura ◽  
Yoshio Kasashima ◽  
Hiroki Ishikawa ◽  
Yasushi Yoshida ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Acid Derivative ◽  
Michael Addition ◽  
Amino Acid Derivative

An efficient and eco-friendly method for the thiol-Michael addition in aqueous solutions using amino acid ionic liquids (AAILs) as organocatalysts

2020 ◽  
Vol 92 (1) ◽  
pp. 97-106
Author(s):  
Roberto Figueroa Guíñez ◽  
José G. Santos ◽  
Ricardo A. Tapia ◽  
Jackson J. Alcazar ◽  
Margarita E. Aliaga ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Ionic Liquids ◽  
Amino Acid ◽  
Efficient Method ◽  
Michael Addition ◽  
Rate Constants ◽  
Michael Reaction ◽  
High Rate ◽  
Reusable Catalyst ◽  
Reaction Conditions

AbstractA series of amino-acid based ionic liquids (Bmim[AA]s) have been synthesized and evaluated as catalysts, in aqueous solution. The results of a kinetic study of the thiol-Michael reaction of L-Cysteine with trans-β-nitrostyrene demonstrated the advantages of using (Bmim[AA]s) as organocatalysts. The benefits include high rate constants; mild reaction conditions; and, a reusable catalyst, which leads to a simple and efficient method for these important kinds of reactions.

Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

1998 ◽  
Vol 51 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin G. Banwell ◽  
Brett D. Bissett ◽  
Chinh T. Bui ◽  
Ha T. T. Pham ◽  
Gregory W. Simpson
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Michael Addition ◽  
Reductive Amination ◽  
Major Product ◽  
Enantioselective Synthesis ◽  
Cyclization Reactions ◽  
Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

Enaminones as Building Blocks In Heterocyclic Synthesis: A New One Pot Synthesis of Polyfunctional Substituted Pyridines

2001 ◽  
Vol 56 (10) ◽  
pp. 1074-1078 ◽  
Author(s):  
Samia Michel Agamy ◽  
Mervat Mohammed Abdel-Khalik ◽  
Mona Hassan Mohamed ◽  
Mohammed Hilmy Elnagdi
Keyword(s):  
Acetic Acid ◽  
Double Bond ◽  
Aromatic Aldehyde ◽  
Michael Addition ◽  
Ammonium Acetate ◽  
Building Blocks ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
Active Methyl ◽  
Substituted Pyridines

Enaminones react with a variety of active methyl and methylene reagents in presence of ammonium acetate to yield functionally substituted pyridines in good yields. The reaction proceeded via initial Michael addition across the double bond followed by cyclization. The reaction of enaminone with aromatic aldehyde in acetic acid/ammonium acetate afforded the dihydropyridine that was oxidized to the corresponding pyridine.

Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(iii) complex

2017 ◽  
Vol 4 (4) ◽  
pp. 573-577 ◽  
Author(s):  
Tao Deng ◽  
Ganesh Kumar Thota ◽  
Yi Li ◽  
Qiang Kang
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Conjugate Addition ◽  
Amino Acid Derivatives ◽  
Highly Efficient

A highly efficient chiral-at-metal Rh(iii) complex catalyzed asymmetric aza-Michael addition was developed, affordingN-protected β-amino acid derivatives with excellent enantioselectivity.

scholarly journals Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

2015 ◽  
Vol 6 (10) ◽  
pp. 1805-1816 ◽  
Author(s):  
Vincent Ladmiral ◽  
Alexandre Charlot ◽  
Mona Semsarilar ◽  
Steven. P. Armes
Keyword(s):  
Amino Acid ◽  
Diblock Copolymer ◽  
Michael Addition ◽  
Self Assembly ◽  
Building Blocks ◽  
Synthesis And Characterization

Two amino acid methacrylates prepared via Michael addition are used as building blocks to prepare novel diblock copolymer nano-objects via polymerisation-induced self-assembly.

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