Literature DB >> 25006984

Remote control of axial chirality: aminocatalytic desymmetrization of N-arylmaleimides via vinylogous Michael addition.

Nicola Di Iorio1, Paolo Righi, Andrea Mazzanti, Michele Mancinelli, Alessia Ciogli, Giorgio Bencivenni.   

Abstract

Remote control of the axial chirality of N-(2-t-butylphenyl)succinimides was realized via the vinylogous Michael addition of 3-substituted cyclohexenones to N-(2-t-butylphenyl)maleimides. 9-Amino(9-deoxy)epi-quinine promoted the enantioselective desymmetrization, leading to atropisomeric succinimides with two adjacent stereocenters.

Entities:  

Year:  2014        PMID： 25006984     DOI： 10.1021/ja505610k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones.

Authors:  Simone Crotti; Giada Belletti; Nicola Di Iorio; Emanuela Marotta; Andrea Mazzanti; Paolo Righi; Giorgio Bencivenni
Journal:  RSC Adv       Date:  2018-09-28       Impact factor: 4.036

2.  Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.

Authors:  Byoungmoo Kim; Alex J Chinn; Daniel R Fandrick; Chris H Senanayake; Robert A Singer; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

3.  Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction.

Authors:  Ji-Wei Zhang; Jin-Hui Xu; Dao-Juan Cheng; Chuan Shi; Xin-Yuan Liu; Bin Tan
Journal:  Nat Commun       Date:  2016-02-11       Impact factor: 14.919

4.  Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles.

Authors:  Lei Zhang; Shao-Hua Xiang; Jun Joelle Wang; Jian Xiao; Jun-Qi Wang; Bin Tan
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

Review 5.  Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.

Authors:  Xiao Xiao; Biao Chen; Yi-Ping Yao; Hai-Jie Zhou; Xu Wang; Neng-Zhong Wang; Fen-Er Chen
Journal:  Molecules       Date:  2022-10-04       Impact factor: 4.927

6.  Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer.

Authors:  Chao Sun; Xiaotian Qi; Xiao-Long Min; Xue-Dan Bai; Peng Liu; Ying He
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

7.  Stereospecific Si-C coupling and remote control of axial chirality by enantioselective palladium-catalyzed hydrosilylation of maleimides.

Authors:  Xing-Wei Gu; Yu-Li Sun; Jia-Le Xie; Xing-Ben Wang; Zheng Xu; Guan-Wu Yin; Li Li; Ke-Fang Yang; Li-Wen Xu
Journal:  Nat Commun       Date:  2020-06-09       Impact factor: 14.919

8.  Computational Investigation on the Origin of Atroposelectivity for the Cinchona Alkaloid Primary Amine-Catalyzed Vinylogous Desymmetrization of N-(2-t-Butylphenyl)maleimides.

Authors:  Nicolò Tampellini; Paolo Righi; Giorgio Bencivenni
Journal:  J Org Chem       Date:  2021-08-04       Impact factor: 4.354
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.