Preparation of enantiopure long chain threo-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids

2006 ◽  
Vol 84 (10) ◽  
pp. 1448-1455 ◽  
Author(s):  
Victoria A Brome ◽  
Laurence M Harwood ◽  
Helen MI Osborn
Keyword(s):  
Amino Acid ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Synthetic Approach ◽  
Alkyl Chains ◽  
Long Chain

The synthetic approach to threo-2-amino-3-hydroxyesters possessing long alkyl chains outlined herein centres on the generation of chiral azomethine ylids by reaction of (5R)-5-phenyl-morpholin-2-one, (R)-(1), with long chain aldehydes. In the presence of a second equivalent of aldehyde, the azomethine ylid can be trapped to afford a cycloadduct with three new stereodefined centres. Degradation of the cycloadduct allows entry to β-substituted-α-amino acid derivatives, which have potential as building blocks for sphingosine synthesis.Key words: sphingosine, morpholinone, chiral azomethine ylid, dipolar cycloaddition.

Photoactive amino acid derivatives with long alkyl chains

Amino Acids ◽  
1996 ◽  
Vol 10 (4) ◽  
pp. 333-343 ◽  
Author(s):  
E. Markava ◽  
G. Matisova ◽  
L. Gerca ◽  
I. Muzikante ◽  
M. Rutkis
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Alkyl Chains

ChemInform Abstract: α-FUNCTIONALIZED AMINO ACID DERIVATIVES. A SYNTHETIC APPROACH OF POSSIBLE BIOGENETIC IMPORTANCE

1980 ◽  
Vol 11 (44) ◽  
Author(s):  
J. D. M. HERSCHEID ◽  
R. J. F. NIVARD ◽  
M. W. TIJHUIS ◽  
H. P. H. SCHOLTEN ◽  
H. C. J. OTTENHEIJM
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Synthetic Approach

.alpha.-Functionalized amino acid derivatives. A synthetic approach of possible biogenetic importance

1980 ◽  
Vol 45 (10) ◽  
pp. 1880-1885 ◽  
Author(s):  
Jacobus D. M. Herscheid ◽  
Rutger J. F. Nivard ◽  
Marian W. Tijhuis ◽  
Henk P. H. Scholten ◽  
Harry C. J. Ottenheijm
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Synthetic Approach

scholarly journals Synthesis of Constrained C ‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

2020 ◽  
Vol 2020 (43) ◽  
pp. 6749-6757
Author(s):  
Florian Rouzier ◽  
Rosanne Sillé ◽  
Ophélie Montiège ◽  
Arnaud Tessier ◽  
Muriel Pipelier ◽  
...  
Keyword(s):  
Amino Acid ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

scholarly journals Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

2009 ◽  
Vol 5 ◽  
Author(s):  
Matthias Breuning ◽  
Tobias Häuser ◽  
Christian Mehler ◽  
Christian Däschlein ◽  
Carsten Strohmann ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
Amino Acid Derivatives ◽  
Chiral Auxiliaries ◽  
Pyrrolidine Ring ◽  
Asymmetric Organocatalysis

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

ChemInform Abstract: Cyclopropyl Building blocks in Organic Synthesis. Part 56. A New and Efficient Access to Oxazoline-5-carboxylates and Amino Acid Derivatives with Cyclopropyl Groups.

ChemInform ◽  
2000 ◽  
Vol 31 (43) ◽  
pp. no-no
Author(s):  
Marcus W. Noetzel ◽  
Markus Tamm ◽  
Thomas Labahn ◽  
Mathias Noltemeyer ◽  
Mazen Es-Sayed ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Amino Acid Derivatives ◽  
Efficient Access

EDA complex directed N-centred radical generation from nitrosoarenes: a divergent synthetic approach

2019 ◽  
Vol 55 (90) ◽  
pp. 13590-13593 ◽  
Author(s):  
Soumen Ghosh ◽  
Gautam Kumar ◽  
Naveen Naveen ◽  
Suman Pradhan ◽  
Indranil Chatterjee
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Synthetic Approach ◽  
Radical Generation ◽  
Eda Complex

N-Centred radicals generated via the formation of EDA complexes are added to electron-deficient allylsulfones to produce isoxazolidines, aziridines or β-amino acid derivatives.

Sign in / Sign up

Export Citation Format

Share Document