Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
21 08 2020
21 08 2020
Historique:
pubmed:
19
8
2020
medline:
7
8
2021
entrez:
19
8
2020
Statut:
ppublish
Résumé
Enallenes can be readily converted into two families of 3.2.0 (hetero)bicycles with high diastereoselectivities through the combination of visible light with a suitable Ir(III) complex (1 mol %). Two complementary pathways, namely, a photocycloaddition versus a radical chain, can then take place. Both manifolds grant complete regiocontrol of the allene difunctionalization. This is accompanied by an original 1,3-group shift using sulfonyl allenamides that deliver a congested tetrasubstituted headbridging carbon in the corresponding product.
Identifiants
pubmed: 32806183
doi: 10.1021/acs.orglett.0c02193
pmc: PMC8010793
doi:
Substances chimiques
Bridged Bicyclo Compounds
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
6354-6359Références
Nat Commun. 2020 May 19;11(1):2509
pubmed: 32427846
J Am Chem Soc. 2019 Aug 28;141(34):13625-13634
pubmed: 31329459
Chem Rev. 2016 Sep 14;116(17):9748-815
pubmed: 27018601
Open Med Chem J. 2008 Apr 15;2:26-37
pubmed: 19696873
Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9468-9472
pubmed: 28640479
Angew Chem Int Ed Engl. 2015 Oct 5;54(41):11918-28
pubmed: 26333192
Chem Sci. 2018 Dec 19;10(8):2315-2319
pubmed: 30881657
Nat Chem. 2017 Sep;9(9):868-873
pubmed: 28837165
J Am Chem Soc. 2019 Nov 6;141(44):17646-17658
pubmed: 31545022
Chem Rev. 2019 Dec 26;119(24):12422-12490
pubmed: 31833759
J Am Chem Soc. 2013 Nov 6;135(44):16610-7
pubmed: 24111991
Angew Chem Int Ed Engl. 2019 Oct 1;58(40):14289-14294
pubmed: 31379035
Chem Sci. 2015 Oct 1;6(10):5426-5434
pubmed: 26668708
J Org Chem. 2007 Jun 8;72(12):4378-89
pubmed: 17489635
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):58-102
pubmed: 26459814
J Am Chem Soc. 2007 Oct 17;129(41):12402-3
pubmed: 17887681
Chem Rev. 2018 Aug 8;118(15):7293-7361
pubmed: 30040389
Chem Sci. 2019 Sep 25;10(44):10297-10304
pubmed: 32110316
Angew Chem Int Ed Engl. 2014 Aug 18;53(34):8991-4
pubmed: 24985967
Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1735-1741
pubmed: 31736186
Chem Soc Rev. 2010 Feb;39(2):783-816
pubmed: 20111793
Angew Chem Int Ed Engl. 2017 Oct 9;56(42):12822-12824
pubmed: 28857371
Angew Chem Int Ed Engl. 2019 Feb 4;58(6):1586-1604
pubmed: 29774651
Angew Chem Int Ed Engl. 2019 Jun 17;58(25):8577-8580
pubmed: 30901148
Angew Chem Int Ed Engl. 2019 May 13;58(20):6703-6707
pubmed: 30875451
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4647-4651
pubmed: 29481716
Angew Chem Int Ed Engl. 2012 Oct 8;51(41):10329-32
pubmed: 22965321
Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10266-10284
pubmed: 31945241
Chem Soc Rev. 2019 Feb 18;48(4):1150-1193
pubmed: 30608075
Angew Chem Int Ed Engl. 2017 Oct 9;56(42):12820-12821
pubmed: 28857385
Acc Chem Res. 2019 May 21;52(5):1301-1312
pubmed: 30985104
J Phys Chem A. 2005 Dec 29;109(51):11902-6
pubmed: 16366641
Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11552-5
pubmed: 23059910
J Am Chem Soc. 2020 Apr 1;142(13):6030-6035
pubmed: 32191462
Angew Chem Int Ed Engl. 2018 May 22;57(21):6242-6246
pubmed: 29624849
ACS Catal. 2013 May 3;3(5):895-902
pubmed: 23691491
J Am Chem Soc. 2020 Feb 5;142(5):2609-2616
pubmed: 31941267
Org Lett. 2018 Jun 1;20(11):3220-3224
pubmed: 29767990
J Am Chem Soc. 2017 Jul 26;139(29):9807-9810
pubmed: 28683547
J Am Chem Soc. 2020 Feb 12;142(6):3094-3103
pubmed: 31927959
Chem Rev. 2016 Sep 14;116(17):9683-747
pubmed: 27120289