Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of donor-acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by Brønsted acid catalysis.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
18 Feb 2021
18 Feb 2021
Historique:
entrez:
25
6
2021
pubmed:
26
6
2021
medline:
26
6
2021
Statut:
epublish
Résumé
Brønsted acid catalyzed formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloadditions of donor-acceptor cyclobutenes, cyclopropenes, and siloxyalkynes with benzopyrylium ions are reported. [4 + 2]-cyclization/deMayo-type ring-extension cascade processes produce highly functionalized benzocyclooctatrienes, benzocycloheptatrienes, and 2-naphthols in good to excellent yields and selectivities. Moreover, the optical purity of reactant donor-acceptor cyclobutenes is fully retained during the cascade. The 1,3-dicarbonyl product framework of the reaction products provides opportunities for salen-type ligand syntheses and the construction of fused pyrazoles and isoxazoles that reveal a novel rotamer-diastereoisomerism.
Identifiants
pubmed: 34168758
doi: 10.1039/d1sc00158b
pii: d1sc00158b
pmc: PMC8179600
doi:
Types de publication
Journal Article
Langues
eng
Pagination
4819-4824Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Angew Chem Int Ed Engl. 2019 Dec 16;58(51):18438-18442
pubmed: 31613040
Chirality. 2010 Oct;22(9):827-37
pubmed: 20803747
Angew Chem Int Ed Engl. 2018 May 28;57(22):6527-6531
pubmed: 29624841
Chem Rev. 2015 Jun 10;115(11):5366-412
pubmed: 25961125
Angew Chem Int Ed Engl. 2012 Jun 18;51(25):6209-13
pubmed: 22588830
Chem Commun (Camb). 2015 Aug 21;51(65):12924-7
pubmed: 26186132
Acc Chem Res. 2017 Oct 17;50(10):2621-2631
pubmed: 28967737
Chem Rec. 2014 Dec;14(6):1070-85
pubmed: 25171137
J Am Chem Soc. 2015 Aug 5;137(30):9579-82
pubmed: 26190818
J Am Chem Soc. 2013 Jul 31;135(30):11402-7
pubmed: 23834249
Chem Sci. 2020 Jul 6;11(30):7957-7962
pubmed: 34094164
J Am Chem Soc. 2019 Nov 6;141(44):17527-17532
pubmed: 31644273
Chemistry. 2006 Jul 24;12(22):5790-805
pubmed: 16710863
J Am Chem Soc. 2005 Mar 2;127(8):2709-16
pubmed: 15725028
Chem Rev. 2013 Jan 9;113(1):PR1-40
pubmed: 23005342
J Am Chem Soc. 2006 Feb 22;128(7):2166-7
pubmed: 16478142
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):10005-8
pubmed: 26136349
J Am Chem Soc. 2004 Jun 23;126(24):7442-3
pubmed: 15198582
J Org Chem. 2006 Apr 28;71(9):3381-8
pubmed: 16626117
Org Lett. 2003 Oct 30;5(22):4121-3
pubmed: 14572264
Chem Rev. 2005 Mar;105(3):857-97
pubmed: 15755079
Angew Chem Int Ed Engl. 2012 Feb 27;51(9):2093-7
pubmed: 22262558
Chem Rev. 2017 Jul 12;117(13):9404-9432
pubmed: 28075115
Chem Rev. 2011 May 11;111(5):3268-333
pubmed: 21488634
Tetrahedron. 2007 Oct 1;63(10):10018-10024
pubmed: 18836512
Org Biomol Chem. 2019 Apr 24;17(17):4183-4195
pubmed: 30924829
Angew Chem Int Ed Engl. 2013 Dec 9;52(50):13284-8
pubmed: 24227689
J Am Chem Soc. 2012 Jun 6;134(22):9062-5
pubmed: 22607029
Phytochemistry. 2008 Mar;69(5):1266-72
pubmed: 18207206
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):456-460
pubmed: 30398303
Angew Chem Int Ed Engl. 2012 Mar 19;51(12):2912-5
pubmed: 22415772
Angew Chem Int Ed Engl. 2019 Aug 5;58(32):10980-10984
pubmed: 31132199
Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14602-14606
pubmed: 28967697
Chem Rev. 2013 Jul 10;113(7):5515-46
pubmed: 23521039
Angew Chem Int Ed Engl. 2014 Apr 14;53(16):4038-40
pubmed: 24596099
J Am Chem Soc. 2013 Mar 27;135(12):4680-3
pubmed: 23472580
Chem Soc Rev. 2017 Aug 29;46(17):5425-5443
pubmed: 28726896
Chem Commun (Camb). 2018 Mar 29;54(27):3375-3378
pubmed: 29547225
Angew Chem Int Ed Engl. 2019 May 13;58(20):6776-6780
pubmed: 30888103
Nat Chem. 2013 May;5(5):423-7
pubmed: 23609094
Chem Rev. 2007 Jan;107(1):239-73
pubmed: 17212476
J Am Chem Soc. 2002 Oct 30;124(43):12650-1
pubmed: 12392398
Chem Asian J. 2010 May 3;5(5):1072-88
pubmed: 20432504
Chem Rev. 2018 Oct 24;118(20):10349-10392
pubmed: 30251840
J Am Chem Soc. 2003 Sep 10;125(36):10921-5
pubmed: 12952473
Chem Rev. 1999 Jan 13;99(1):27-76
pubmed: 11848980
Angew Chem Int Ed Engl. 2018 Oct 22;57(43):14225-14229
pubmed: 30178906
J Am Chem Soc. 2004 Mar 24;126(11):3529-33
pubmed: 15025480
J Am Chem Soc. 2015 Jan 21;137(2):560-3
pubmed: 25551644
J Am Chem Soc. 2002 Dec 18;124(50):14836-7
pubmed: 12475311
Chemistry. 2017 Jul 3;23(37):8780-8799
pubmed: 28295709
Acc Chem Res. 2014 Apr 15;47(4):1396-405
pubmed: 24650430
Chem Rev. 1999 Mar 10;99(3):881-930
pubmed: 11749434
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15794-8
pubmed: 26768697
Acc Chem Res. 2017 Nov 21;50(11):2776-2788
pubmed: 29112367
J Am Chem Soc. 2007 Aug 22;129(33):10096-7
pubmed: 17663557
Angew Chem Int Ed Engl. 2016 Apr 25;55(18):5573-6
pubmed: 27006138
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):14222-14226
pubmed: 28816392
Angew Chem Int Ed Engl. 2009;48(43):8129-32
pubmed: 19774585
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7479-7483
pubmed: 28493594
Chemistry. 2015 Dec 7;21(50):18122-7
pubmed: 26515732
J Am Chem Soc. 2005 Jul 6;127(26):9342-3
pubmed: 15984841
Org Lett. 2020 Apr 3;22(7):2645-2650
pubmed: 32208616
J Am Chem Soc. 2009 Feb 18;131(6):2090-1
pubmed: 19161254
Angew Chem Int Ed Engl. 2016 Sep 5;55(37):11153-7
pubmed: 27440757
Org Lett. 2004 May 27;6(11):1745-8
pubmed: 15151404
Chem Soc Rev. 2013 Feb 7;42(3):902-23
pubmed: 23172010