Regulation of Axial Chirality through Dynamic Covalent Bond Constrained Biaryls.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
30 Jun 2019
30 Jun 2019
Historique:
received:
03
05
2019
accepted:
24
05
2019
entrez:
29
8
2019
pubmed:
29
8
2019
medline:
29
8
2019
Statut:
epublish
Résumé
A strategy of dynamic covalent chemistry within constrained biaryls was developed for the modulation of axial chirality. The ring fusion partners of amide and aldehyde allowed the manipulation of ring/chain equilibrium and chirality transfer within cyclic diastereomeric hemiaminal. Dynamic covalent reactions (DCRs) with alcohols, thiols, and secondary amines further enabled the reversal of chirality relay and thereby regulation of axial chirality. Moreover, a combination of NMR, X-ray, and density functional theory results shed light on the structural basis of chirality transfer, exhibiting modest to excellent diastereoselectivity under thermodynamic control. The critical role of the amide unit in the modulation of axial chirality was also corroborated. Finally, the chiroptical signal was controlled through changing solvents, DCRs, and stimuli-responsive switching of DCRs.
Identifiants
pubmed: 31460119
doi: 10.1021/acsomega.9b01273
pmc: PMC6648723
doi:
Types de publication
Journal Article
Langues
eng
Pagination
10273-10278Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
Chem Rev. 2000 May 10;100(5):1789-1816
pubmed: 11777421
Angew Chem Int Ed Engl. 2002 Mar 15;41(6):898-952
pubmed: 12491278
Angew Chem Int Ed Engl. 2005 Aug 26;44(34):5384-427
pubmed: 16116589
Chem Rev. 2006 Sep;106(9):3652-711
pubmed: 16967917
Org Lett. 2007 Mar 1;9(5):899-902
pubmed: 17284047
J Am Chem Soc. 2008 Dec 10;130(49):16812-22
pubmed: 19554697
Chem Soc Rev. 2011 Jan;40(1):258-71
pubmed: 20938496
Chem Rev. 2011 Feb 9;111(2):563-639
pubmed: 20939606
ChemMedChem. 2011 Mar 7;6(3):505-13
pubmed: 21360821
J Am Chem Soc. 2013 Jun 26;135(25):9222-39
pubmed: 23731408
Chem Soc Rev. 2013 Aug 21;42(16):6634-54
pubmed: 23749182
Chem Soc Rev. 2014 Mar 21;43(6):1948-62
pubmed: 24287608
Chem Soc Rev. 2014 Mar 21;43(6):1873-84
pubmed: 24445841
J Am Chem Soc. 2014 Mar 26;136(12):4480-3
pubmed: 24666208
ACS Nano. 2014 Aug 26;8(8):8074-81
pubmed: 24960454
Angew Chem Int Ed Engl. 2014 Sep 26;53(40):10641-4
pubmed: 25132625
Angew Chem Int Ed Engl. 2015 Mar 9;54(11):3276-89
pubmed: 25582911
Chem Rev. 2015 Aug 12;115(15):7543-88
pubmed: 25697681
Nat Chem. 2015 Mar;7(3):234-40
pubmed: 25698333
Chem Rev. 2015 Aug 12;115(15):7001-45
pubmed: 25813093
Chem Soc Rev. 2015 Jun 7;44(11):3418-30
pubmed: 25904287
Chem Rev. 2015 Aug 12;115(15):8001-37
pubmed: 25974371
Angew Chem Int Ed Engl. 2015 Sep 21;54(39):11338-49
pubmed: 26096635
Chem Rev. 2015 Aug 12;115(15):7304-97
pubmed: 26189453
Org Lett. 2015 Aug 21;17(16):4098-101
pubmed: 26263248
Chem Rev. 2015 Sep 23;115(18):10081-206
pubmed: 26346838
Chem Rev. 2015 Oct 28;115(20):11239-300
pubmed: 26414162
Nat Chem. 2016 Feb;8(2):138-43
pubmed: 26791896
Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4130-54
pubmed: 26894262
Chem Commun (Camb). 2016 May 1;52(35):5932-5
pubmed: 27054507
J Am Chem Soc. 2016 Jun 8;138(22):6956-9
pubmed: 27218264
J Am Chem Soc. 2016 Jul 20;138(28):8912-9
pubmed: 27345035
Chem Rev. 2016 Nov 23;116(22):13752-13990
pubmed: 27754649
J Am Chem Soc. 2016 Nov 23;138(46):15142-15145
pubmed: 27933887
J Am Chem Soc. 2017 Feb 15;139(6):2474-2483
pubmed: 28145690
Chem Rev. 2017 Mar 8;117(5):4528-4561
pubmed: 28164696
J Am Chem Soc. 2017 Sep 13;139(36):12459-12465
pubmed: 28749147
Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1300-1305
pubmed: 29239090
Adv Mater. 2018 Feb;30(8):
pubmed: 29265677
Angew Chem Int Ed Engl. 2018 Feb 5;57(6):1627-1631
pubmed: 29285875
Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3777-3781
pubmed: 29437283
J Am Chem Soc. 2018 Apr 25;140(16):5334-5338
pubmed: 29652488
Acc Chem Res. 2018 May 15;51(5):1153-1163
pubmed: 29694014
J Am Chem Soc. 2018 May 23;140(20):6432-6440
pubmed: 29756777
J Am Chem Soc. 2018 Jul 5;140(26):8064-8068
pubmed: 29920089
Chem Commun (Camb). 2018 Jul 12;54(57):7991-7994
pubmed: 29966026
Proc Natl Acad Sci U S A. 2018 Sep 18;115(38):9414-9422
pubmed: 30012601
J Am Chem Soc. 2018 Aug 15;140(32):10344-10353
pubmed: 30024156
J Am Chem Soc. 2018 Aug 29;140(34):10839-10847
pubmed: 30067898
J Org Chem. 2018 Sep 7;83(17):9858-9869
pubmed: 30091361
Nat Chem. 2018 Oct;10(10):1031-1036
pubmed: 30104723
J Am Chem Soc. 2018 Sep 26;140(38):12239-12246
pubmed: 30156414
J Am Chem Soc. 2018 Oct 24;140(42):13558-13561
pubmed: 30303001
Chem Soc Rev. 2018 Nov 26;47(23):8525-8540
pubmed: 30375584
J Am Chem Soc. 2018 Nov 21;140(46):15577-15581
pubmed: 30398863
J Am Chem Soc. 2018 Dec 12;140(49):17278-17289
pubmed: 30458108