ChemInform Abstract: Stereocontrolled Transformation of Cyclohexene β-Amino Esters into syn- or anti-Difunctionalized Acyclic β2,3-Amino Acid Derivatives.

ChemInform ◽  
2014 ◽  
Vol 45 (34) ◽  
pp. no-no
Author(s):  
Maria Cherepanova ◽  
Lorand Kiss ◽  
Ferenc Fueloep
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Amino Esters

Transition metal-free aerobic oxidative cleavage of the C–N bonds of α-amino esters

2019 ◽  
Vol 6 (23) ◽  
pp. 3854-3858
Author(s):  
Shenpeng Tan ◽  
Feng Li ◽  
Soojun Park ◽  
Sanghee Kim
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Metal Catalysts ◽  
Oxidative Cleavage ◽  
Amino Acid Derivatives ◽  
Metal Free ◽  
Amino Esters

A base-mediated aerobic oxidative cleavage of α-amino esters involving a hydroperoxide intermediate was reported, which represents the first example of the cleavage of the α-C–N bonds of amino acid derivatives without the aid of metal catalysts.

An insight into the synthesis of novel aryl-substituted alicyclic β-amino acid derivatives through substrate-directed palladium-catalysed regio- and stereoselective cross-coupling

RSC Advances ◽  
2015 ◽  
Vol 5 (18) ◽  
pp. 13628-13634 ◽  
Author(s):  
Melinda Nonn ◽  
Loránd Kiss ◽  
Mikko M. Hänninen ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acid ◽  
Cross Coupling ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Aryl Iodides ◽  
Insight Into

Novel aryl-substituted alicyclic β-amino acid derivatives were synthesized through substrate-determined palladium-catalysed cross-coupling of aryl iodides with five- or six-membered cycloalkene β-amino esters.

Synthesis and Chiroptical Properties of Some N-(2-Chloro-7-cyclopropyl-4,7-dihydro-4-oxo-thieno[2,3-b]pyridine-5-carbonyl) L-α-Amino Esters

1997 ◽  
Vol 52 (3) ◽  
pp. 419-426 ◽  
Author(s):  
Mustafa M. El-Abadelah ◽  
Musa Z. Nazer ◽  
Salim S. Sabri ◽  
Salim M. Khalil ◽  
Wolfgang Voelter ◽  
...  
Keyword(s):  
Amino Acid ◽  
Spectral Data ◽  
Cotton Effect ◽  
Amino Acid Derivatives ◽  
Cd Spectra ◽  
Conformational Isomerism ◽  
Chiroptical Properties ◽  
Amino Esters ◽  
Sign Inversion ◽  
Carbonyl Chloride

Abstract A series of N-(2-chloro-7-cyclopropyl-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carbonyl)-L-α-amino esters (5 ) have been prepared via the respective thieno[2,3-b]pyridinyl-5-carbonyl chloride (4). The CD spectra of the L-aliphatic (5a -d ) and L-aromatic (5e-g) a-amino acid derivatives display, in organic solvents, sign inversion of the measured Cotton effect (CE) bands. This chiroptical behaviour is probably associated with differences in conformational isomerism of either set. MS and NMR spectral data of the title compounds are presented.

Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

Synlett ◽  
2021 ◽  
Author(s):  
Loránd Kiss ◽  
Melinda Nonn ◽  
Lamiaa Ouchakour ◽  
Attila M. Remete
Keyword(s):  
Amino Acid ◽  
Current Account ◽  
Ring Opening ◽  
Reductive Amination ◽  
Piperidine Ring ◽  
Ring Cleavage ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Biological Potential ◽  
The Current Account

AbstractThe current Account gives an insight into the synthesis of some N-heterocyclic β-amino acid derivatives and various functionalized saturated azaheterocycles accessed from substituted cycloalkenes via ring C=C bond oxidative cleavage followed by ring closing across double reductive amination. The ring-cleavage protocol has been accomplished according to two common approaches: a) Os-catalyzed dihydroxylation/NaIO4 vicinal diol oxidation and b) ozonolysis. A comparative study on these methodologies has been investigated. Due to the everincreasing relevance of organofluorine chemistry in drug research as well as of the high biological potential of β-amino acid derivatives several illustrative examples to the access of various fluorine-containing piperidine or azepane β-amino acid derivatives are also presented in the current Account.1 Introduction2 Olefin-Bond Transformation by Oxidative Ring Cleavage3 Synthesis of Saturated Azaheterocycles via Oxidative Ring-Opening/Ring-Closing Double Reductive Amination3.1 Importance of Fluorine-Containing Azaheterocycles in Pharmaceutical Research3.2 Synthesis of Azaheterocyclic Amino Acid Derivatives with a Piperidine or Azepane Framework through Oxidative Ring Opening/Reductive Amination3.2.1 Synthesis of Piperidine β-Amino Esters3.2.2 Synthesis of Azepane β-Amino Esters3.2.3 Synthesis of Fluorine-Containing Piperidine γ-Amino Esters3.3 Synthesis of Tetrahydroisoquinoline Derivatives through Oxidative Ring Opening/Reductive Amination Protocol3.4 Synthesis of Functionalized Benzazepines through Reductive Amination3.4.1 Synthesis of Benzo[c]azepines3.4.2 Synthesis of Benzo[d]azepines3.5 Synthesis of Various N-Heterocycles via Ozonolysis/Reductive Amination3.5.1 Synthesis of Compounds with an Azepane Ring3.5.2 Synthesis of Piperidine β-Amino Acids and Piperidine-Fused β-Lactams3.5.3 Synthesis of γ-Lactams with a Piperidine Ring3.5.4 Synthesis of other N-Heterocycles4 Summary and Outlook5 List of Abbreviations

scholarly journals Enantioselective Synthesis of anti-β-Hydroxy-α-amino Esters via an Organocatalyzed Decarboxylative Aldol Reaction

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1295-1299 ◽  
Author(s):  
Yoshiji Takemoto ◽  
Taryn March ◽  
Akihiro Murata ◽  
Yusuke Kobayashi
Keyword(s):  
Amino Acid ◽  
Malonic Acid ◽  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Combined Use ◽  
Aldol Addition ◽  
High Yields ◽  
Pentafluorobenzoic Acid

The first enantioselective decarboxylative aldol addition with α-amido-substituted malonic acid half oxyesters (MAHOs) is described. The combined use of a newly designed bifunctional sulfonamide catalyst with pentafluorobenzoic acid as an additive afforded the β-hydroxy-α-amino acid derivatives in moderate to high yields and with high enantioselectivities.

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