Dimerizing cascades of enallenamides reveal the visible-light-promoted activation of cumulated C-C double bonds.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
02 Mar 2022
02 Mar 2022
Historique:
received:
01
12
2021
accepted:
25
01
2022
entrez:
28
3
2022
pubmed:
29
3
2022
medline:
29
3
2022
Statut:
epublish
Résumé
The visible-light-promoted activation of conjugated C-C double bonds is well developed, while that of cumulated systems is underexplored. We present the feasibility of this challenging approach. The localization of a triplet on an allenamide arm can be favored over that on a conjugated alkene. Allenamides with an arylacryloyl arm dimerize at room temperature in the presence of visible light and an iridium(iii) photocatalyst. Two orthogonal polycyclizations took place and their outcome is entirely dictated by the substitution of the alkene partner. Both cascades afford complex molecular architectures with high selectivity. Products form through the ordered rearrangement of twelve π electrons, providing a [3.2.0] bicyclic unit tethered to a fused tricycle, whose formation included an aryl C-H functionalization step, using disubstituted alkenes. The outcome was reverted with trisubstituted ones, which gave rise to taxane-like bridged tricycles that had two six-membered lactams flanking a cyclooctane ring, which was established through the creation of four alternate C-C bonds.
Identifiants
pubmed: 35340858
doi: 10.1039/d1sc06719b
pii: d1sc06719b
pmc: PMC8890112
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2632-2639Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Chem Sci. 2021 Jul 9;12(31):10643-10648
pubmed: 34447557
Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15407-15410
pubmed: 28994229
Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1881-1884
pubmed: 28097790
Acc Chem Res. 2019 Feb 19;52(2):465-479
pubmed: 30640446
Angew Chem Int Ed Engl. 2019 Feb 4;58(6):1586-1604
pubmed: 29774651
J Am Chem Soc. 2021 Jul 28;143(29):11209-11217
pubmed: 34279085
Angew Chem Int Ed Engl. 2012 Oct 8;51(41):10329-32
pubmed: 22965321
Nature. 1994 Feb 17;367(6464):630-4
pubmed: 7906395
Org Lett. 2015 Aug 7;17(15):3892-4
pubmed: 26186274
Org Lett. 2021 Aug 20;23(16):6536-6541
pubmed: 34369150
J Am Chem Soc. 2019 Nov 6;141(44):17646-17658
pubmed: 31545022
J Am Chem Soc. 2021 Nov 17;143(45):18952-18959
pubmed: 34738467
Front Physiol. 2018 Mar 26;9:254
pubmed: 29632493
Chem Sci. 2019 Sep 25;10(44):10297-10304
pubmed: 32110316
J Am Chem Soc. 2020 Jun 10;142(23):10526-10533
pubmed: 32406238
Angew Chem Int Ed Engl. 2017 Jan 2;56(1):319-323
pubmed: 27900830
Angew Chem Int Ed Engl. 2014 Aug 18;53(34):8991-4
pubmed: 24985967
Org Lett. 2006 Aug 31;8(18):4031-3
pubmed: 16928066
Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7817-20
pubmed: 22740322
Nature. 2016 Nov 10;539(7628):268-271
pubmed: 27732585
Chemistry. 2020 May 15;26(28):6141-6146
pubmed: 32270524
Angew Chem Int Ed Engl. 2014 Nov 17;53(47):12921-4
pubmed: 25251714
Chem Soc Rev. 2014 May 7;43(9):3003-40
pubmed: 24500088
Chem Soc Rev. 2010 Feb;39(2):783-816
pubmed: 20111793
J Org Chem. 2016 Aug 19;81(16):6898-926
pubmed: 27477076
Chem Sci. 2021 Jun 23;12(28):9673-9681
pubmed: 34349938
Chem Rev. 2020 Jul 8;120(13):5910-5953
pubmed: 32343125
J Org Chem. 2012 Dec 21;77(24):11096-100
pubmed: 23198916
Nat Prod Rep. 2021 Mar 1;38(3):470-488
pubmed: 32895676
Angew Chem Int Ed Engl. 2019 May 13;58(20):6703-6707
pubmed: 30875451
Acc Chem Res. 2016 Sep 20;49(9):1997-2006
pubmed: 27588818
Chem Rev. 2018 Aug 22;118(16):7532-7585
pubmed: 30011194
Chem Rev. 2020 Dec 23;120(24):13545-13598
pubmed: 33301308
Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9468-9472
pubmed: 28640479
Chem Rev. 2013 Jul 10;113(7):4862-904
pubmed: 23550917
Science. 2021 Mar 26;371(6536):1338-1345
pubmed: 33766881
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7661-4
pubmed: 24888463
J Am Chem Soc. 2021 Aug 25;143(33):13441-13449
pubmed: 34398603
Med Res Rev. 2015 Jan;35(1):1-62
pubmed: 24827545
Chem Sci. 2018 Dec 19;10(8):2315-2319
pubmed: 30881657
Org Lett. 2020 Aug 21;22(16):6354-6359
pubmed: 32806183
Chem Soc Rev. 2021 Jul 7;50(13):7359-7377
pubmed: 34013927
Acc Chem Res. 2016 Aug 16;49(8):1566-77
pubmed: 27482835
Angew Chem Int Ed Engl. 2012 Mar 26;51(13):3074-112
pubmed: 22271630
Chem Rev. 2016 Sep 14;116(17):9683-747
pubmed: 27120289
Angew Chem Int Ed Engl. 2020 Jan 2;59(1):436-441
pubmed: 31650679
J Am Chem Soc. 2013 Nov 6;135(44):16610-7
pubmed: 24111991
Chem Rev. 2022 Jan 26;122(2):1626-1653
pubmed: 34227803