DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
05 11 2021
05 11 2021
Historique:
pubmed:
21
10
2021
medline:
27
1
2022
entrez:
20
10
2021
Statut:
ppublish
Résumé
A pair of chiral bis(amidine) [BAM] proton complexes provide reagent (catalyst)-controlled, highly diastereo- and enantioselective direct aza-Henry reactions leading to α-alkyl-substituted α,β-diamino esters. A
Identifiants
pubmed: 34669416
doi: 10.1021/acs.joc.1c02112
pmc: PMC8899924
mid: NIHMS1781822
doi:
Substances chimiques
Acids
0
Esters
0
Indicators and Reagents
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
15606-15617Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM084333
Pays : United States
Références
J Am Chem Soc. 2006 Mar 29;128(12):3928-30
pubmed: 16551098
J Am Chem Soc. 2013 Aug 14;135(32):11799-802
pubmed: 23906087
Org Process Res Dev. 2016 Feb 19;20(2):215-226
pubmed: 27065720
J Am Chem Soc. 2007 Mar 28;129(12):3466-7
pubmed: 17341075
J Am Chem Soc. 2008 May 7;130(18):5866-7
pubmed: 18410096
Nat Chem. 2018 Nov;10(11):1164-1170
pubmed: 30150723
J Phys Chem B. 2009 May 7;113(18):6378-96
pubmed: 19366259
J Am Chem Soc. 2010 Mar 10;132(9):2880-2
pubmed: 20151644
Org Lett. 2020 Nov 6;22(21):8496-8499
pubmed: 33054232
Org Lett. 2014 Jun 6;16(11):3146-9
pubmed: 24828455
Org Lett. 2009 Aug 6;11(15):3310-3
pubmed: 19583199
J Am Chem Soc. 2007 Sep 5;129(35):10632-3
pubmed: 17691788
J Am Chem Soc. 2001 Jun 20;123(24):5843-4
pubmed: 11403635
Acc Chem Res. 2004 Aug;37(8):506-17
pubmed: 15311949
J Am Chem Soc. 2008 Aug 20;130(33):10878-9
pubmed: 18646755
Org Lett. 2006 Aug 3;8(16):3533-6
pubmed: 16869653
Chem Rev. 2005 Aug;105(8):3167-96
pubmed: 16092828
Nat Commun. 2017 Mar 20;8:14793
pubmed: 28317928
J Am Chem Soc. 2008 Dec 3;130(48):16150-1
pubmed: 19006300
Chem Rev. 2018 May 23;118(10):5080-5200
pubmed: 29676895
Org Lett. 2015 Feb 20;17(4):880-3
pubmed: 25697748
Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789
pubmed: 9944570
J Am Chem Soc. 2016 Oct 26;138(42):13794-13797
pubmed: 27749040
J Comput Chem. 2006 Nov 30;27(15):1787-99
pubmed: 16955487
Science. 2013 May 31;340(6136):1065-8
pubmed: 23723229
Chem Commun (Camb). 2012 Jun 7;48(45):5578-80
pubmed: 22543734
J Med Chem. 1984 Jun;27(6):713-7
pubmed: 6737413
Science. 2018 Aug 17;361(6403):664-667
pubmed: 30115803
Org Biomol Chem. 2016 Oct 12;14(40):9588-9597
pubmed: 27714327
Chem Commun (Camb). 2008 Sep 21;(35):4177-9
pubmed: 18802521
J Phys Chem A. 2013 Nov 27;117(47):12590-600
pubmed: 24147965
J Am Chem Soc. 2004 Mar 24;126(11):3418-9
pubmed: 15025457
Chem Sci. 2011 Jan 1;2(6):1076-1079
pubmed: 22708054
Beilstein J Org Chem. 2015 Dec 14;11:2577-83
pubmed: 26734103
Chemistry. 2010 Jan 25;16(4):1153-7
pubmed: 20024985
J Am Chem Soc. 2008 Feb 20;130(7):2170-1
pubmed: 18225906
Nature. 2010 Jun 24;465(7301):1027-32
pubmed: 20577205
J Org Chem. 2016 Apr 15;81(8):3286-95
pubmed: 27008440
J Am Chem Soc. 2007 Apr 25;129(16):4900-1
pubmed: 17394322
J Pept Sci. 2003 Nov-Dec;9(11-12):666-78
pubmed: 14658788
Angew Chem Int Ed Engl. 2014 Aug 4;53(32):8411-5
pubmed: 24985050
Chem Soc Rev. 2009 Jul;38(7):1940-8
pubmed: 19551174
Acc Chem Res. 2004 Aug;37(8):518-25
pubmed: 15311950
Chem Rev. 2013 May 8;113(5):2887-939
pubmed: 23461586
Org Biomol Chem. 2013 May 21;11(19):3223-9
pubmed: 23584159
Chem Sci. 2018 Jan 31;9(8):2336-2339
pubmed: 29719706
J Am Chem Soc. 2017 Apr 26;139(16):5627-5639
pubmed: 28384402
J Med Chem. 2013 Jul 25;56(14):5974-8
pubmed: 23789888
J Comput Aided Mol Des. 1995 Feb;9(1):87-110
pubmed: 7751872
Molecules. 2010 Mar 04;15(3):1280-90
pubmed: 20335980
Science. 2019 Apr 5;364(6435):45-51
pubmed: 30948544
J Med Chem. 1978 Aug;21(8):746-53
pubmed: 691000
J Am Chem Soc. 2008 Nov 5;130(44):14362-3
pubmed: 18841892
Org Lett. 2010 Dec 17;12(24):5744-7
pubmed: 21090654
Nature. 2016 Apr 21;532(7599):353-6
pubmed: 27018656
Org Lett. 2012 Dec 21;14(24):6322-5
pubmed: 23214987
Org Lett. 2008 Oct 16;10(20):4397-400
pubmed: 18798639
Angew Chem Int Ed Engl. 2007;46(23):4222-66
pubmed: 17525926
J Am Chem Soc. 2007 Jan 31;129(4):768-9
pubmed: 17243806
Org Biomol Chem. 2005 Apr 21;3(8):1362-4
pubmed: 15827627
Chemistry. 2008;14(27):8094-7
pubmed: 18655092
Chemistry. 2017 May 11;23(27):6464-6482
pubmed: 27859806