Carbohydrate-Based Chiral Iodoarene Catalysts: A Survey through the Development of an Improved Catalyst Design.
Mitsunobu reaction
asymmetric catalysis
benzylic substitution
bulky substituent
carbohydrate
dearomatization
iodoarene
organocatalysis
spirolactonization
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
28 Oct 2019
28 Oct 2019
Historique:
received:
09
10
2019
revised:
24
10
2019
accepted:
24
10
2019
entrez:
31
10
2019
pubmed:
31
10
2019
medline:
14
3
2020
Statut:
epublish
Résumé
Iodoarene catalysts can be applied in versatile reactions, for instance in the construction of complex chiral molecules via dearomatization of simple aromatic compounds. Recently, we reported the synthesis of the first carbohydrate-based chiral iodoarene catalysts and their application in asymmetric catalysis. Here we describe the synthesis of some new and improved catalysts. An account on how we got to the improved catalyst design, as well as the X-ray structure of one of the carbohydrate-based iodoarenes, is given.
Identifiants
pubmed: 31661915
pii: molecules24213883
doi: 10.3390/molecules24213883
pmc: PMC6864689
pii:
doi:
Substances chimiques
Carbohydrates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Déclaration de conflit d'intérêts
The authors declare no conflicts of interest.
Références
J Org Chem. 2017 Dec 1;82(23):12701-12714
pubmed: 29087187
Angew Chem Int Ed Engl. 2012 Dec 14;51(51):12662-86
pubmed: 23208999
Chemistry. 2013 Dec 16;19(51):17244-60
pubmed: 24272963
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):413-7
pubmed: 26596513
Org Biomol Chem. 2015 Oct 7;13(37):9637-58
pubmed: 26264193
Carbohydr Res. 2015 Jun 26;411:56-63
pubmed: 25974854
Angew Chem Int Ed Engl. 2008;47(20):3787-90
pubmed: 18393265
Angew Chem Int Ed Engl. 2011 Apr 26;50(18):4068-93
pubmed: 21506209
Molecules. 2016 Dec 10;21(12):
pubmed: 27973420
Nature. 2008 Sep 18;455(7211):304-8
pubmed: 18800128
Beilstein J Org Chem. 2018 Aug 8;14:2082-2089
pubmed: 30202461
J Org Chem. 2003 Jun 13;68(12):4615-30
pubmed: 12790564
Beilstein J Org Chem. 2018 May 30;14:1244-1262
pubmed: 29977393
Nature. 2008 Sep 18;455(7211):314-22
pubmed: 18800130
J Am Chem Soc. 2011 Dec 7;133(48):19386-92
pubmed: 22026511
Beilstein J Org Chem. 2016 Jan 29;12:166-71
pubmed: 26877819
Chem Commun (Camb). 2011 Aug 7;47(29):8379-81
pubmed: 21701750
Beilstein J Org Chem. 2012;8:1219-26
pubmed: 23019451