Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

2014 ◽  
Vol 2014 (17) ◽  
pp. 3599-3606 ◽  
Author(s):  
Maksim Ošeka ◽  
Artur Noole ◽  
Sergei Žari ◽  
Mario Öeren ◽  
Ivar Järving ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Derivatives Of

ChemInform Abstract: Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Maksim Oseka ◽  
Artur Noole ◽  
Sergei Zari ◽  
Mario Oeeren ◽  
Ivar Jaerving ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Derivatives Of

Diastereoselective synthesis of α-aminoalkylphosphonic acid derivatives of Betti base

2014 ◽  
Vol 63 (6) ◽  
pp. 1390-1394 ◽  
Author(s):  
K. E. Metlushka ◽  
D. N. Sadkova ◽  
L. N. Shaimardanova ◽  
K. A. Nikitina ◽  
A. I. Tufatullin ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Betti Base ◽  
Aminoalkylphosphonic Acid ◽  
Derivatives Of

Aminophosphonates and aminophosphonic acids with tetrasubstituted stereogenic center: diastereoselective synthesis from cyclic ketimines

2019 ◽  
Vol 17 (31) ◽  
pp. 7352-7359 ◽  
Author(s):  
Jakub Iwanejko ◽  
Anna Brol ◽  
Bartłomiej M. Szyja ◽  
Marek Daszkiewicz ◽  
Elżbieta Wojaczyńska ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Aminophosphonic Acid ◽  
Aminophosphonic Acids ◽  
Stereogenic Center ◽  
Derivatives Of

Chiral tetrasubstituted aminophosphonic acid derivatives of hexahydroquinoxalin-2(1H)-one were synthesised via diastereoselective hydrophosphonylation of corresponding imines with tris(trimethylsilyl)phosphite as phosphorus nucleophile.

Diastereoselective synthesis of spiro derivatives of 3-substituted 2,3,4,4a,5,6-hexahydro-1H-benzo[c]quinolizines

2009 ◽  
Vol 45 (5) ◽  
pp. 743-754 ◽  
Author(s):  
T. V. Glukhareva ◽  
E. V. Deeva ◽  
A. Yu. Platonova ◽  
I. V. Geide ◽  
M. I. Kodess ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Spiro Derivatives ◽  
Derivatives Of

ChemInform Abstract: Diastereoselective Synthesis of Spiro Derivatives of 3-Substituted 2,3,4,4a,5,6-Hexahydro-1H-benzo[c]quinolizines.

ChemInform ◽  
2010 ◽  
Vol 41 (8) ◽  
Author(s):  
T. V. Glukhareva ◽  
E. V. Deeva ◽  
A. Yu. Platonova ◽  
I. V. Geide ◽  
M. I. Kodess ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Spiro Derivatives ◽  
Derivatives Of

Diastereoselective synthesis of trans-fused tetrahydropyran derivatives of 5H-dibenzo[a,d]cycloheptene

2002 ◽  
Vol 43 (48) ◽  
pp. 8697-8700 ◽  
Author(s):  
Hua Mao ◽  
Mohamed Koukni ◽  
Tomasz Kozlecki ◽  
Frans Compernolle ◽  
Georges J. Hoornaert
Keyword(s):  
Diastereoselective Synthesis ◽  
Derivatives Of

Photo aldol reactions with 5-methoxyoxazoles: Highly regio- and diastereoselective synthesis of α-amino β-hydroxy carboxylic acid derivatives

2003 ◽  
Vol 81 (6) ◽  
pp. 555-559 ◽  
Author(s):  
Axel G Griesbeck ◽  
Samir Bondock
Keyword(s):  
Aldol Reactions ◽  
Diastereoselective Synthesis ◽  
Hydroxy Carboxylic Acid ◽  
Electronically Excited ◽  
Methoxy Substituent ◽  
Hydroxy Esters ◽  
High Yields ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Very High

A versatile route to derivatives of α-amino β-hydroxy carboxylic acids, either with tertiary (from a corresponding glycine equivalent) or a quaternary α-carbon center is described. The key reaction is the cycloaddition of electronically excited carbonyl compounds (aromatic and aliphatic aldehydes, respectively) to oxazoles. To make the products hydrolytically more labile, a methoxy substituent at position C-5 was introduced leading to the formation of cycloadducts with an orthoester substructure. The photocycloaddition, either with triplet excited (aromatic) carbonyls or with singlet excited (aliphatic) carbonyls, led to the formation of mixtures of endo- and exo-diastereoisomers with moderate to very high exo-selectivities. The 4-unsubstituted 5-methoxyoxazole 1 (glycine equivalent) gave the [2 + 2]-adducts 3a–3f with aldehydes 2a–2f in high yields and excellent diastereoselectivities. Hydrolysis of these compounds resulted in the α-amino β-hydroxy esters 4a–4f with preferred erythro (S*,S*) configuration. As an extension of this process, 4-alkylated 5-methoxyoxazoles 5a–5f were applied as alkene components and the corresponding cycloadducts with benzaldehyde 6a–6f were obtained. Again, the exo-diastereoisomers were formed as the major products in diastereoselectivities from 73:27 (exo:endo) up to >95:5. Hydrolysis of these adducts resulted in the formation of α-amino β-hydroxy esters 7a–7f with like (S*,S*) configuration of the major diastereoisomers.Key words: photo aldol reaction, oxazoles, oxetanes, photocycloaddition, amino acids, hydroxy acids.

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