Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis.
chromanes
fluorine
gauche effect
organocatalysis
stereospecificity
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:
24 08 2020
24 08 2020
Historique:
received:
09
04
2020
pubmed:
30
4
2020
medline:
30
4
2020
entrez:
30
4
2020
Statut:
ppublish
Résumé
The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF
Identifiants
pubmed: 32347605
doi: 10.1002/anie.202005181
pmc: PMC7496101
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
15069-15075Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
Org Lett. 2018 Dec 21;20(24):8073-8076
pubmed: 30525706
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
Chembiochem. 2004 May 3;5(5):637-43
pubmed: 15122635
J Med Chem. 2018 Jul 26;61(14):5822-5880
pubmed: 29400967
Acc Chem Res. 2018 Jul 17;51(7):1701-1710
pubmed: 29894155
Bioorg Med Chem. 2001 Dec;9(12):3207-13
pubmed: 11711296
Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2175-7
pubmed: 20196156
Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2469-73
pubmed: 23362120
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. 2010 Sep 17;49(39):7068-71
pubmed: 20718062
Chem Commun (Camb). 2012 Jun 14;48(47):5877-9
pubmed: 22569949
Chem Commun (Camb). 2007 Jun 28;(24):2521-3
pubmed: 17563816
J Am Chem Soc. 2018 Nov 14;140(45):15206-15218
pubmed: 30350956
Science. 2011 Dec 23;334(6063):1681-4
pubmed: 22194571
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
J Org Chem. 2001 Jan 12;66(1):59-65
pubmed: 11429930
J Org Chem. 2017 Nov 17;82(22):11721-11726
pubmed: 28695730
Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9215-8
pubmed: 23873650
Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9266-70
pubmed: 23852804
Chemistry. 2017 May 2;23(25):6142-6149
pubmed: 27788283
Chemistry. 2015 Mar 27;21(14):5561-83
pubmed: 25711981
J Am Chem Soc. 2018 May 16;140(19):6039-6043
pubmed: 29708750
FASEB J. 1999 Jul;13(10):1145-55
pubmed: 10385606
J Am Chem Soc. 2016 Oct 26;138(42):13858-13861
pubmed: 27709922
Beilstein J Org Chem. 2018 May 9;14:1021-1027
pubmed: 29977374
Mar Drugs. 2012 Mar;10(3):639-654
pubmed: 22611360
J Am Chem Soc. 2018 Apr 11;140(14):4797-4802
pubmed: 29583001
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
Cancer Res. 2001 Jan 1;61(1):118-25
pubmed: 11196148
Chem Soc Rev. 2016 Nov 7;45(22):6270-6288
pubmed: 27417189
Chem Commun (Camb). 2018 Oct 23;54(85):12002-12005
pubmed: 30221278
Org Lett. 2019 Jul 5;21(13):4919-4923
pubmed: 30963766
Org Lett. 2007 May 10;9(10):1995-8
pubmed: 17417863
J Am Chem Soc. 2017 Mar 29;139(12):4354-4357
pubmed: 28277652
Expert Opin Pharmacother. 2000 Dec;1(7):1413-21
pubmed: 11249474
Chem Rev. 2016 Mar 9;116(5):3328-435
pubmed: 26861673
Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8214-64
pubmed: 23873766
Chemistry. 2016 Jun 20;22(26):8728-39
pubmed: 27061937
Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14911-4
pubmed: 26450355
Angew Chem Int Ed Engl. 2010 Nov 8;49(46):8724-8
pubmed: 20886497
Org Biomol Chem. 2016 Feb 7;14(5):1805-13
pubmed: 26757679
J Am Chem Soc. 2016 Apr 20;138(15):5000-3
pubmed: 27046019
J Invest Dermatol. 2013 May;133(5):1351-60
pubmed: 23303451
J Med Chem. 2015 Nov 25;58(22):9041-60
pubmed: 26523333
Chem Soc Rev. 2008 Feb;37(2):320-30
pubmed: 18197348
J Org Chem. 2013 May 3;78(9):4463-72
pubmed: 23611174
Science. 2016 Jul 1;353(6294):51-4
pubmed: 27365443
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