Stereocontrolled Synthesis of Fluorinated Isochromans via Iodine(I)/Iodine(III) Catalysis.
Fluorination
Heterocycles
Hypervalent Iodine
Isosteres
Stereoelectronic Effects
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
25 07 2022
25 07 2022
Historique:
received:
11
04
2022
pubmed:
11
5
2022
medline:
22
7
2022
entrez:
10
5
2022
Statut:
ppublish
Résumé
The success of saturated, fluorinated heterocycles in contemporary drug discovery provides a stimulus for creative endeavor in main group catalysis. Motivated by the ubiquity of isochromans across the bioactive small molecule spectrum, the prominence of the anomeric effect in regulating conformation, and the metabolic lability of the benzylic position, iodine(I)/iodine(III) catalysis has been leveraged for the stereocontrolled generation of selectively fluorinated analogs. To augment the current arsenal of fluorocyclization reactions involving carboxylic acid derivatives, the reaction of readily accessible 2-vinyl benzaldehydes is disclosed (up to >95 : 05 d.r. and 97 : 03 e.r.). Key stereoelectronic interactions manifest themselves in the X-ray crystal structures of the products, thereby validating the [CH
Identifiants
pubmed: 35536157
doi: 10.1002/anie.202205277
pmc: PMC9401867
doi:
Substances chimiques
Iodides
0
Iodine
9679TC07X4
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202205277Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Chem Soc Rev. 2021 Jul 19;50(14):8178-8192
pubmed: 34060550
Chem Rev. 2014 Oct 22;114(20):10476-526
pubmed: 25303539
Beilstein J Org Chem. 2018 May 9;14:1021-1027
pubmed: 29977374
Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13760-4
pubmed: 25298130
Chem Rev. 2019 Dec 26;119(24):12033-12088
pubmed: 31741377
Angew Chem Int Ed Engl. 2020 Aug 24;59(35):15069-15075
pubmed: 32347605
J Med Chem. 2018 Jul 26;61(14):5822-5880
pubmed: 29400967
Acc Chem Res. 2018 Jul 17;51(7):1701-1710
pubmed: 29894155
J Med Chem. 1996 Jun 21;39(13):2435-7
pubmed: 8691438
Chem Rev. 2016 Mar 9;116(5):3328-435
pubmed: 26861673
Nat Chem. 2018 Apr;10(4):383-394
pubmed: 29568051
J Am Chem Soc. 2016 Apr 20;138(15):5004-7
pubmed: 26978593
Angew Chem Int Ed Engl. 2018 Dec 10;57(50):16431-16435
pubmed: 30255972
Angew Chem Int Ed Engl. 2007;46(19):3410-49
pubmed: 17427893
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
ACS Med Chem Lett. 2021 Jul 16;12(8):1220-1229
pubmed: 34413951
J Am Chem Soc. 2018 Nov 14;140(45):15206-15218
pubmed: 30350956
J Org Chem. 2017 Nov 17;82(22):11792-11798
pubmed: 28752759
Angew Chem Int Ed Engl. 2011 Dec 9;50(50):11860-71
pubmed: 21953782
Angew Chem Int Ed Engl. 2019 Sep 2;58(36):12486-12490
pubmed: 31295383
Beilstein J Org Chem. 2018 Jul 18;14:1813-1825
pubmed: 30112085
J Am Chem Soc. 2016 Oct 26;138(42):13858-13861
pubmed: 27709922
Chem Soc Rev. 2014 Jan 7;43(1):135-47
pubmed: 24162874
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):413-7
pubmed: 26596513
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15642-82
pubmed: 26630449
Angew Chem Int Ed Engl. 2021 Jun 7;60(24):13647-13651
pubmed: 33721384
Chem Soc Rev. 2016 Nov 7;45(22):6270-6288
pubmed: 27417189
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):422-6
pubmed: 26553478
Chem Sci. 2021 Jun 29;12(32):10686-10695
pubmed: 34476053
Nat Chem Biol. 2010 Jul;6(7):482-3
pubmed: 20559312
J Med Chem. 2009 Nov 12;52(21):6752-6
pubmed: 19827778
Angew Chem Int Ed Engl. 2017 Dec 22;56(52):16669-16673
pubmed: 29143469
Angew Chem Int Ed Engl. 2015 Jul 20;54(30):8653-7
pubmed: 26095789
Angew Chem Int Ed Engl. 2022 Jul 25;61(30):e202205277
pubmed: 35536157
Org Biomol Chem. 2018 Aug 1;16(30):5386-5402
pubmed: 30024581
J Am Chem Soc. 2020 Nov 25;142(47):20048-20057
pubmed: 33191747
Nature. 2009 Jul 9;460(7252):197-201
pubmed: 19587760
Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14911-4
pubmed: 26450355
J Am Chem Soc. 2018 Oct 10;140(40):13034-13041
pubmed: 30183276
ACS Omega. 2020 Apr 22;5(19):10633-10640
pubmed: 32455181
Chem Rev. 2016 Jan 27;116(2):422-518
pubmed: 26756377
J Am Chem Soc. 2016 Apr 20;138(15):5000-3
pubmed: 27046019
Chemistry. 2021 May 3;27(25):7193-7213
pubmed: 33512034
Chemistry. 2016 Mar 7;22(11):3660-4
pubmed: 26641801
Chem Soc Rev. 2008 Feb;37(2):320-30
pubmed: 18197348
Science. 2007 Sep 28;317(5846):1881-6
pubmed: 17901324
Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8533-7
pubmed: 26069071
Chem Soc Rev. 2008 Feb;37(2):308-19
pubmed: 18197347
J Med Chem. 2011 Apr 28;54(8):2529-91
pubmed: 21413808