scholarly journals Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides

2017 ◽  
Vol 13 ◽  
pp. 1518-1523 ◽  
Author(s):  
Ryota Miyaji ◽  
Yuuki Wada ◽  
Akira Matsumoto ◽  
Keisuke Asano ◽  
Seijiro Matsubara
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Enantioselective Synthesis ◽  
Chiral Compounds ◽  
Axially Chiral ◽  
Electrophilic Bromination ◽  
Mechanistic Investigations ◽  
Molecular Skeleton

Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out.

scholarly journals Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu‐Catalyzed Atroposelective Aryl Amination

2020 ◽  
Vol 59 (23) ◽  
pp. 8844-8848 ◽  
Author(s):  
Johanna Frey ◽  
Alaleh Malekafzali ◽  
Isabel Delso ◽  
Sabine Choppin ◽  
Françoise Colobert ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Compounds ◽  
Aryl Amination ◽  
Axially Chiral

scholarly journals Asymmetric Synthesis of N-N Axially Chiral Compounds via Organocatalytic Atroposelective N-Acylation

2021 ◽  
Author(s):  
Wei Lin ◽  
Qun Zhao ◽  
Yao Li ◽  
Ming Pan ◽  
Chen Yang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Acylation Reaction ◽  
Axial Chirality ◽  
Chiral Compounds ◽  
Axially Chiral

Compared with the well-developed C-C and C-N axial chirality, asymmetric synthesis of N-N axial chirality remains elusive and challenging. Herein we report the first atroposelective N-acylation reaction of quinazolinone type benzamides...

scholarly journals Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu‐Catalyzed Atroposelective Aryl Amination

2020 ◽  
Vol 132 (23) ◽  
pp. 8929-8933 ◽  
Author(s):  
Johanna Frey ◽  
Alaleh Malekafzali ◽  
Isabel Delso ◽  
Sabine Choppin ◽  
Françoise Colobert ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Compounds ◽  
Aryl Amination ◽  
Axially Chiral

scholarly journals Organocatalytic atroposelective heterocycloaddition to access axially chiral 2-arylquinolines

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Gongming Yang ◽  
Shaofa Sun ◽  
Zhipeng Li ◽  
Yuhan Liu ◽  
Jian Wang
Keyword(s):  
Drug Discovery ◽  
Asymmetric Synthesis ◽  
Vital Role ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Chiral Amine ◽  
New Class ◽  
Axially Chiral ◽  
High Yields

AbstractAxially chiral heterobiaryls play a vital role in asymmetric synthesis and drug discovery. However, there are few reports on the synthesis of atropisomeric heterobiaryls compared with axially chiral biaryls. Thus, the rapid enantioselective construction of optically active heterobiaryls and their analogues remains an attractive challenge. Here, we report a concise chiral amine-catalyzed atroposelective heterocycloaddition reaction of alkynes with ortho-aminoarylaldehydes, and obtain a new class of axially chiral 2-arylquinoline skeletons with high yields and excellent enantioselectivities. In addition, the axially chiral 2-arylquinoline framework with different substituents is expected to be widely used in enantioselective synthesis.

scholarly journals Copper Hydride-Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes

2019 ◽  
Author(s):  
Liela Bayeh ◽  
Stephen L. Buchwald
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
Hydroxyl Groups ◽  
Copper Hydride ◽  
Selective Synthesis ◽  
Keto Ester ◽  
Axially Chiral ◽  
Conjugated Enynes ◽  
Proton Source

The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride-catalyzed semi-reduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of mono-deuterated allenes and chiral 2,5-dihydropyrroles are described.

scholarly journals Copper Hydride-Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes

2019 ◽  
Author(s):  
Liela Bayeh ◽  
Stephen L. Buchwald
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Enantioselective Synthesis ◽  
Hydroxyl Groups ◽  
Copper Hydride ◽  
Selective Synthesis ◽  
Keto Ester ◽  
Axially Chiral ◽  
Conjugated Enynes ◽  
Proton Source

The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride-catalyzed semi-reduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of mono-deuterated allenes and chiral 2,5-dihydropyrroles are described.

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