Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids

2017 ◽  
Vol 15 (36) ◽  
pp. 7705-7709 ◽  
Author(s):  
Margarita Cantú-Reyes ◽  
Isabel Alvarado-Beltrán ◽  
Ricardo Ballinas-Indilí ◽  
Cecilio Álvarez-Toledano ◽  
Marcos Hernández-Rodríguez
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Mannich Reaction ◽  
Lewis Base ◽  
One Pot ◽  
Ketene Acetals

Synthesis of chiral β2,2,3-amino acids. Either Lewis acid or Lewis base promote the reaction, surprisingly, each activation afford different enantiomer.

scholarly journals Tartaric Acid–Zinc Nitrate as an Efficient Brønsted Acid-Assisted Lewis Acid Catalyst for the Mannich Reaction

2018 ◽  
Vol 42 (9) ◽  
pp. 463-466 ◽  
Author(s):  
Hao Dong ◽  
Qing Liu ◽  
Yuanyu Tian ◽  
Yingyun Qiao
Keyword(s):  
Tartaric Acid ◽  
Lewis Acid ◽  
Mannich Reaction ◽  
Reaction Times ◽  
Acid Catalyst ◽  
Zinc Nitrate ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Brönsted Acid

Tartaric acid–zinc nitrate has been found to be an efficient Brønsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Brønsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.

Enantioselective aldol reaction of silyl ketene acetals promoted by a Lewis base-activated Lewis acid catalyst

2009 ◽  
Vol 20 (12) ◽  
pp. 1369-1370 ◽  
Author(s):  
Yasushi Shimoda ◽  
Teppei Tando ◽  
Shunsuke Kotani ◽  
Masaharu Sugiura ◽  
Makoto Nakajima
Keyword(s):  
Lewis Acid ◽  
Aldol Reaction ◽  
Acid Catalyst ◽  
Lewis Base ◽  
Lewis Acid Catalyst ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

ChemInform Abstract: Enantioselective Aldol Reaction of Silyl Ketene Acetals Promoted by a Lewis Base-Activated Lewis Acid Catalyst.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yasushi Shimoda ◽  
Teppei Tando ◽  
Shunsuke Kotani ◽  
Masaharu Sugiura ◽  
Makoto Nakajima
Keyword(s):  
Lewis Acid ◽  
Aldol Reaction ◽  
Acid Catalyst ◽  
Lewis Base ◽  
Lewis Acid Catalyst ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

scholarly journals A Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

2021 ◽  
Author(s):  
Lamiaa Reda Ahmed ◽  
Ahmed F. M. EL-Mahdy ◽  
Cheng-Tang Pan ◽  
Shiao-Wei Kuo
Keyword(s):  
Amino Acids ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
One Pot ◽  
Covalent Organic Framework ◽  
The One ◽  
Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

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