Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing anortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines

2015 ◽  
Vol 17 (21) ◽  
pp. 5180-5183 ◽  
Author(s):  
Mi Tang ◽  
Lingfeng Tong ◽  
Lei Ju ◽  
Wanwan Zhai ◽  
Yang Hu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Benzoic Acid ◽  
Aromatic Aldehydes ◽  
Michael Acceptor ◽  
Acid Catalyzed

Critical role of Bronsted acid in Lewis-acid-catalyzed synthesis of Amadori and Heyns compounds of β-amino acids

2021 ◽  
pp. 1-11
Author(s):  
Debasree Chanda ◽  
Gangothri M. Venkataswamy ◽  
Lagamawwa V. Hipparagi ◽  
Nanishankar V. Harohally
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Critical Role ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

scholarly journals Synthesis of new Cα-tetrasubstituted α-amino acids

2009 ◽  
Vol 5 ◽  
Author(s):  
Andreas A Grauer ◽  
Burkhard König
Keyword(s):  
Amino Acids ◽  
Secondary Structure ◽  
Aromatic Aldehydes ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Peptide Backbone ◽  
Aliphatic Aldehydes ◽  
New Class ◽  
Cyclic Amino Acids

Cα-Tetrasubstituted α-amino acids are important building blocks for the synthesis of peptidemimetics with stabilized secondary structure, because of their ability to rigidify the peptide backbone. Recently our group reported a new class of cyclic Cα-tetrasubstituted tetrahydrofuran α-amino acids prepared from methionine and aromatic aldehydes. We now report the extension of this methodology to aliphatic aldehydes. Although such aldehydes are prone to give aldol products under the reaction conditions used, we were able to obtain the target cyclic amino acids in low to moderate yields and in some cases with good diastereoselectivity.

Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane

2010 ◽  
Vol 80 (5) ◽  
pp. 964-967 ◽  
Author(s):  
N. R. Ishkulova ◽  
L. E. Oparina ◽  
L. B. Kochetova ◽  
T. P. Kustova ◽  
N. V. Kalinina ◽  
...  
Keyword(s):  
Amino Acids ◽  
Benzoic Acid ◽  
Aqueous Dioxane ◽  
Acid Esters

The question of Friedel-Crafts transformylations. Acid-catalyzed reactions of aromatic aldehydes with arenes

1987 ◽  
Vol 52 (8) ◽  
pp. 1591-1599 ◽  
Author(s):  
Royston M. Roberts ◽  
Ahmed M. El-Khawaga ◽  
Kevin M. Sweeney ◽  
Maher F. El-Zohry
Keyword(s):  
Aromatic Aldehydes ◽  
Acid Catalyzed ◽  
Catalyzed Reactions
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