A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
07 Jun 2020
07 Jun 2020
Historique:
received:
25
03
2020
accepted:
14
05
2020
entrez:
3
9
2020
pubmed:
3
9
2020
medline:
3
9
2020
Statut:
epublish
Résumé
An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent
Identifiants
pubmed: 32874501
doi: 10.1039/d0sc01729a
pii: d0sc01729a
pmc: PMC7444369
doi:
Types de publication
Journal Article
Langues
eng
Pagination
5572-5576Informations de copyright
This journal is © The Royal Society of Chemistry 2020.
Références
Acc Chem Res. 2009 Jun 16;42(6):756-68
pubmed: 19371087
Beilstein J Org Chem. 2011;7:582-95
pubmed: 21647256
Nat Chem. 2019 Sep;11(9):768-778
pubmed: 31444486
J Org Chem. 2018 Mar 16;83(6):3385-3391
pubmed: 29512387
J Chem Theory Comput. 2010 Jun 8;6(6):1825-33
pubmed: 26615842
Chem Pharm Bull (Tokyo). 2016;64(7):704-17
pubmed: 27373626
Chemistry. 2017 Jan 12;23(3):554-557
pubmed: 27862459
Angew Chem Int Ed Engl. 1998 Nov 2;37(20):2848-2850
pubmed: 29711099
J Am Chem Soc. 2006 Feb 1;128(4):1222-32
pubmed: 16433539
Angew Chem Int Ed Engl. 2010 Nov 22;49(48):9254-7
pubmed: 20979074
J Phys Chem A. 2010 Dec 2;114(47):12531-9
pubmed: 21050022
Chemistry. 2017 Apr 3;23(19):4547-4550
pubmed: 28326640
J Am Chem Soc. 2018 Sep 26;140(38):12216-12225
pubmed: 30215516
Org Lett. 2013 Jul 5;15(13):3448-51
pubmed: 23772965
Chem Sci. 2017 Jan 1;8(1):606-610
pubmed: 28451207
Chemistry. 2015 Mar 16;21(12):4800-4
pubmed: 25676870
Org Lett. 2014 Aug 15;16(16):4256-9
pubmed: 25075571
J Am Chem Soc. 2011 Nov 9;133(44):17934-41
pubmed: 21936561
J Org Chem. 2017 Dec 1;82(23):12655-12668
pubmed: 29096432
Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11114-8
pubmed: 24039087
Org Lett. 2011 Aug 19;13(16):4426-9
pubmed: 21786836
J Org Chem. 2011 Oct 7;76(19):7849-59
pubmed: 21916401
Bioorg Med Chem Lett. 2000 Aug 7;10(15):1637-40
pubmed: 10937713
J Am Chem Soc. 2013 Aug 21;135(33):12160-3
pubmed: 23909371
J Org Chem. 2009 Jun 5;74(11):4055-60
pubmed: 19391608
Eur J Med Chem. 2008 Nov;43(11):2279-90
pubmed: 18639369
Chem Rev. 2014 Sep 24;114(18):8807-64
pubmed: 25144663
J Med Chem. 2000 Jun 15;43(12):2324-31
pubmed: 10882358
Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8551-4
pubmed: 22807228
Org Biomol Chem. 2019 Feb 27;17(9):2331-2335
pubmed: 30734817
Org Lett. 2011 Mar 4;13(5):892-5
pubmed: 21302920
J Am Chem Soc. 2015 Apr 29;137(16):5320-3
pubmed: 25856510
Org Lett. 2017 Dec 1;19(23):6324-6327
pubmed: 29152981