Modular synthesis of non-conjugated
Alkene Functionalization
Alkenes
Directing group
Grubbs catalyst
Olefin metathesis
Journal
Tetrahedron
ISSN: 0040-4020
Titre abrégé: Tetrahedron
Pays: England
ID NLM: 2984170R
Informations de publication
Date de publication:
30 Jul 2021
30 Jul 2021
Historique:
entrez:
16
8
2021
pubmed:
17
8
2021
medline:
17
8
2021
Statut:
ppublish
Résumé
We report a direct and modular method to access non-conjugated alkenyl amides containing the 8-aminoquinoline (AQ) directing auxiliary and related groups via cross-metathesis. In this way, readily available, AQ-containing, terminal β,γ-unsaturated amides can be coupled with various terminal alkenes to furnish internal alkene products that are otherwise difficult to prepare. The value of this family of products stems from their ability to participate in a number of directed alkene functionalization reactions.
Identifiants
pubmed: 34393281
doi: 10.1016/j.tet.2021.132279
pmc: PMC8360400
mid: NIHMS1720450
pii:
doi:
Types de publication
Journal Article
Langues
eng
Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM125052
Pays : United States
Références
Acc Chem Res. 2009 Aug 18;42(8):1074-86
pubmed: 19552413
J Am Chem Soc. 2018 May 2;140(17):5805-5813
pubmed: 29630359
Angew Chem Int Ed Engl. 2019 Mar 18;58(12):3923-3927
pubmed: 30729619
J Am Chem Soc. 2016 May 11;138(18):5805-8
pubmed: 27093112
J Am Chem Soc. 2018 Aug 1;140(30):9332-9336
pubmed: 29925236
Org Lett. 2020 Jun 5;22(11):4333-4338
pubmed: 32401533
Nat Commun. 2020 Dec 22;11(1):6432
pubmed: 33353940
Org Lett. 2019 Nov 15;21(22):8915-8920
pubmed: 31687830
Org Lett. 2021 May 7;23(9):3620-3625
pubmed: 33851845
Chem Sci. 2018 Jul 18;9(33):6839-6843
pubmed: 30310616
Angew Chem Int Ed Engl. 2011 Mar 7;50(11):2450-94
pubmed: 21365719
Org Lett. 2020 Jan 17;22(2):694-699
pubmed: 31913642
Org Lett. 2020 May 1;22(9):3524-3530
pubmed: 32294385
ACS Catal. 2021 Apr 2;11(7):4239-4246
pubmed: 34422450
J Am Chem Soc. 2003 Sep 17;125(37):11360-70
pubmed: 16220959
J Am Chem Soc. 2018 Dec 12;140(49):16929-16935
pubmed: 30421921
Org Biomol Chem. 2019 Jul 21;17(27):6607-6611
pubmed: 31237304
J Am Chem Soc. 2017 Aug 16;139(32):11261-11270
pubmed: 28727452
Chem Sci. 2018 May 16;9(23):5278-5283
pubmed: 29997883
Org Lett. 2016 Oct 7;18(19):5014-5017
pubmed: 27650477
Angew Chem Int Ed Engl. 2013 Nov 4;52(45):11726-43
pubmed: 24105797
J Am Chem Soc. 2018 Mar 14;140(10):3542-3546
pubmed: 29474067
J Am Chem Soc. 2021 Jan 20;143(2):1195-1202
pubmed: 33378201
Org Lett. 2018 Jul 6;20(13):3853-3857
pubmed: 29888604
J Am Chem Soc. 2019 Nov 20;141(46):18475-18485
pubmed: 31600069
J Am Chem Soc. 2019 Jun 5;141(22):8758-8763
pubmed: 31083939
Org Lett. 2020 Nov 20;22(22):9022-9028
pubmed: 33151076
Angew Chem Int Ed Engl. 2012 Mar 5;51(10):2382-6
pubmed: 22287529
ACS Catal. 2019 Apr 5;9(4):3260-3265
pubmed: 31799023
J Am Chem Soc. 2019 Jun 26;141(25):10048-10059
pubmed: 31150208
Chem Sci. 2019 Jul 3;10(34):7952-7957
pubmed: 31853350
Chem Sci. 2020 Sep 22;11(41):11307-11314
pubmed: 35382446
J Am Chem Soc. 2017 Aug 9;139(31):10657-10660
pubmed: 28738150
Angew Chem Int Ed Engl. 2019 Nov 18;58(47):17068-17073
pubmed: 31538388
Nat Commun. 2019 Nov 5;10(1):5025
pubmed: 31690717
J Am Chem Soc. 2018 Mar 7;140(9):3223-3227
pubmed: 29384373
J Org Chem. 2020 Jan 17;85(2):774-787
pubmed: 31829008
Chem Commun (Camb). 2019 Aug 29;55(71):10523-10526
pubmed: 31415048
Chem Sci. 2018 Sep 6;9(44):8363-8368
pubmed: 30542583
J Am Chem Soc. 2020 Dec 2;142(48):20470-20480
pubmed: 33205955
J Am Chem Soc. 2016 Nov 9;138(44):14705-14712
pubmed: 27709911
J Am Chem Soc. 2016 Nov 23;138(46):15122-15125
pubmed: 27779861