Synthesis of Axially Chiral Amino Acid and Amino Alcohols via Additive−Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent Transformations of the Product Amidoaza[5]helicene

2010 ◽  
Vol 75 (20) ◽  
pp. 7010-7013 ◽  
Author(s):  
Takumi Furuta ◽  
Junya Yamamoto ◽  
Yuki Kitamura ◽  
Ayano Hashimoto ◽  
Hyuma Masu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Coupling Reaction ◽  
Amino Alcohols ◽  
Axially Chiral ◽  
Ligand Free

Axially Chiral Bis(α-amino Acid)s and Their Deamino Analogues. Synthesis and Configurational Assignment

1998 ◽  
Vol 63 (2) ◽  
pp. 211-221 ◽  
Author(s):  
Miloš Tichý ◽  
Luděk Ridvan ◽  
Miloš Buděšínský ◽  
Jiří Závada ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Amino Acid ◽  
Nmr Spectra ◽  
Building Blocks ◽  
X Ray Diffraction ◽  
Amino Groups ◽  
X Ray ◽  
Configurational Assignment ◽  
Symmetry Properties ◽  
Axially Chiral ◽  
Polymeric Structures

The axially chiral bis(α-amino acid)s cis-2 and trans-2 as possible building blocks for polymeric structures of novel type of helicity were prepared. Their configuration has been determined by NMR spectroscopy and, in the case of the trans-isomer, confirmed by single-crystal X-ray diffraction. Analogous pair of stereoisomeric diacids cis-3 and trans-3, devoid of the amino groups, was also prepared and their configuration assigned. The observed differences in the NMR spectra of cis- and trans-isomers of 2 and 3 are discussed from the viewpoint of their different symmetry properties.

scholarly journals Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3223
Author(s):  
Ji-Wei Zhang ◽  
Shao-Hua Xiang ◽  
Shaoyu Li ◽  
Bin Tan
Keyword(s):  
Amino Alcohols ◽  
Sigmatropic Rearrangement ◽  
Synthetic Route ◽  
Mild Conditions ◽  
Good Substrate ◽  
Diaryliodonium Salts ◽  
Axially Chiral

NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

Ligand-Free Copper Powder Catalyzed Direct Coupling Reaction of Heterocyclic C–H Bonds and Aryl Halides

Synthesis ◽  
2012 ◽  
Vol 44 (19) ◽  
pp. 3027-3032 ◽  
Author(s):  
Yu Yuan ◽  
Ying Han ◽  
Xiaohu Wang ◽  
Xiaowei Wang ◽  
Liangzhong Lv ◽  
...  
Keyword(s):  
Copper Powder ◽  
Coupling Reaction ◽  
Direct Coupling ◽  
Aryl Halides ◽  
Ligand Free

Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

2014 ◽  
Vol 79 (12) ◽  
pp. 5608-5616 ◽  
Author(s):  
Tapobrata Mitra ◽  
Saibal Jana ◽  
Sharmila Pandey ◽  
Prabuddha Bhattacharya ◽  
Uttam K. Khamrai ◽  
...  
Keyword(s):  
Amino Acid ◽  
Axially Chiral

Ligand-free Cu-catalyzed O-arylation of aliphatic diols

RSC Advances ◽  
2015 ◽  
Vol 5 (81) ◽  
pp. 66104-66108 ◽  
Author(s):  
Yufen Zheng ◽  
Wenxing Zou ◽  
Laichun Luo ◽  
Jiabei Chen ◽  
Songwen Lin ◽  
...  
Keyword(s):  
Copper Catalyst ◽  
Scale Up ◽  
Coupling Reaction ◽  
Aryl Iodides ◽  
Ligand Free

Coupling reaction between aryl iodides with aliphatic diols was realized with a ligand-free copper catalyst. This method was successfully applied in the process of scale-up synthesis of medicinal candidate product EMB-3.

Ligand-free CuI-catalyzed selective C–N coupling of aliphatic amino group of α-amino acid amides with ortho-dihaloarenes

2013 ◽  
Vol 54 (45) ◽  
pp. 6045-6048 ◽  
Author(s):  
Yan Wang ◽  
Xingzhao Tu ◽  
Xirui Lv ◽  
Lihong Zhou ◽  
Qingle Zeng
Keyword(s):  
Amino Acid ◽  
Amino Group ◽  
Ligand Free

Spontaneous symmetry breaking during interrupted crystallization of an axially chiral amino acid derivative

2010 ◽  
Vol 46 (12) ◽  
pp. 2094 ◽  
Author(s):  
Mark A. Sephton ◽  
Christopher R. Emerson ◽  
Lev N. Zakharov ◽  
Paul R. Blakemore
Keyword(s):  
Amino Acid ◽  
Symmetry Breaking ◽  
Spontaneous Symmetry Breaking ◽  
Acid Derivative ◽  
Amino Acid Derivative ◽  
Axially Chiral
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