Literature DB >> 27259076

Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Modulation of Enantiomeric Excess.

Thomas M Bräuer1, Qi Zhang1, Konrad Tiefenbacher2.   

Abstract

The noncovalent combination of a supramolecular host with iminium organocatalysis is described. Due to cation-π interactions the reactive iminium species is held inside the host and reacts in this confined environment. The products formed differ up to 92 % ee from the control experiments without added host. A model rationalizing the observed difference is presented.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords:  enantioselectivity; host-guest systems; iminium catalysis; organocatalysis; supramolecular chemistry

Year:  2016        PMID： 27259076     DOI： 10.1002/anie.201602382

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  17 in total

1.  Binding Properties and Supramolecular Polymerization of a Water-Soluble Resorcin[4]arene.

Authors:  Jacobs H Jordan; Anthony Wishard; Joel T Mague; Bruce C Gibb
Journal:  Org Chem Front       Date:  2019-03-21       Impact factor: 5.281

2.  Combining iminium and supramolecular catalysis for the [4 + 2] cycloaddition of E-cinnamaldehydes.

Authors:  Kendra K Shrestha; Michael A Hilyard; Indunil Alahakoon; Michael C Young
Journal:  Org Biomol Chem       Date:  2022-08-24       Impact factor: 3.890

3.  Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength.

Authors:  Sebastian Benz; Jiri Mareda; Céline Besnard; Naomi Sakai; Stefan Matile
Journal:  Chem Sci       Date:  2017-10-16       Impact factor: 9.825

4.  Anion-π catalysis: bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces.

Authors:  Le Liu; Yoann Cotelle; Juliane Klehr; Naomi Sakai; Thomas R Ward; Stefan Matile
Journal:  Chem Sci       Date:  2017-03-17       Impact factor: 9.825

5.  To catalyze or not to catalyze: elucidation of the subtle differences between the hexameric capsules of pyrogallolarene and resorcinarene.

Authors:  Qi Zhang; Lorenzo Catti; Ville R I Kaila; Konrad Tiefenbacher
Journal:  Chem Sci       Date:  2016-11-15       Impact factor: 9.825

6.  Host-guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies.

Authors:  Rakesh Puttreddy; Ngong Kodiah Beyeh; S Maryamdokht Taimoory; Daniel Meister; John F Trant; Kari Rissanen
Journal:  Beilstein J Org Chem       Date:  2018-07-10       Impact factor: 2.883

7.  Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host.

Authors:  Alexander R Nödling; Katarzyna Świderek; Raquel Castillo; Jonathan W Hall; Antonio Angelastro; Louis C Morrill; Yi Jin; Yu-Hsuan Tsai; Vicent Moliner; Louis Y P Luk
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-23       Impact factor: 15.336

8.  Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.

Authors:  Jan Wallbaum; Lennart K B Garve; Peter G Jones; Daniel B Werz
Journal:  Chemistry       Date:  2016-11-29       Impact factor: 5.236

9.  Optimized iminium-catalysed 1,4-reductions inside the resorcinarene capsule: achieving >90% ee with proline as catalyst.

Authors:  Daria Sokolova; Konrad Tiefenbacher
Journal:  RSC Adv       Date:  2021-07-14       Impact factor: 4.036

10.  Catalysis with Pnictogen, Chalcogen, and Halogen Bonds.

Authors:  Sebastian Benz; Amalia I Poblador-Bahamonde; Nicolas Low-Ders; Stefan Matile
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-20       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.