Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives.
Amino Acids
/ chemistry
Carbon
/ chemistry
Catalysis
Chemistry Techniques, Synthetic
Chemistry, Pharmaceutical
/ methods
Drug Design
Imines
/ chemistry
Molecular Structure
Nitrogen
/ chemistry
Organophosphonates
/ chemical synthesis
Palladium
/ chemistry
Phosphorous Acids
/ analysis
Phosphorus
/ chemistry
Rhodium
/ chemistry
Stereoisomerism
asymmetric synthesis
diastereoselective
enantioselective
tetrasubstituted carbons
α-aminophosphonates
α-aminophosphonic acid
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
27 May 2021
27 May 2021
Historique:
received:
30
04
2021
revised:
22
05
2021
accepted:
24
05
2021
entrez:
2
6
2021
pubmed:
3
6
2021
medline:
24
7
2021
Statut:
epublish
Résumé
Due to their structural similarity with natural α-amino acids, α-aminophosphonic acid derivatives are known biologically active molecules. In view of the relevance of tetrasubstituted carbons in nature and medicine and the strong dependence of the biological activity of chiral molecules into their absolute configuration, the synthesis of α-aminophosphonates bearing tetrasubstituted carbons in an asymmetric fashion has grown in interest in the past few decades. In the following lines, the existing literatures for the synthesis of optically active tetrasubstituted α-aminophosphonates are summarized, comprising diastereoselective and enantioselective approaches.
Identifiants
pubmed: 34071844
pii: molecules26113202
doi: 10.3390/molecules26113202
pmc: PMC8199250
pii:
doi:
Substances chimiques
Amino Acids
0
Imines
0
Organophosphonates
0
Phosphorous Acids
0
phosphonic acid
13598-36-2
Phosphorus
27YLU75U4W
Palladium
5TWQ1V240M
Carbon
7440-44-0
Rhodium
DMK383DSAC
Nitrogen
N762921K75
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Eusko Jaurlaritza
ID : IT 992-16
Organisme : Ministerio de Economía, Industria y Competitividad, Gobierno de España
ID : CTQ-2015-67871R
Références
Chem Commun (Camb). 2016 Sep 18;52(72):10882-5
pubmed: 27530154
Angew Chem Int Ed Engl. 2014 Feb 10;53(7):1862-6
pubmed: 24420101
J Med Chem. 2015 Mar 12;58(5):2350-7
pubmed: 25699713
Org Biomol Chem. 2014 Mar 14;12(10):1595-602
pubmed: 24469542
Angew Chem Int Ed Engl. 2011 Jun 27;50(27):5998-6000
pubmed: 21612008
Bioorg Chem. 2016 Dec;69:132-139
pubmed: 27816796
Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8785-8789
pubmed: 28557241
J Am Chem Soc. 2016 May 18;138(19):6194-203
pubmed: 27092817
Org Lett. 2019 Dec 6;21(23):9473-9477
pubmed: 31729883
Chem Rev. 2007 Nov;107(11):4584-671
pubmed: 17915933
Acc Chem Res. 2004 Aug;37(8):506-17
pubmed: 15311949
Antibiot Med Biotekhnol. 1987 Jan;32(1):66-75
pubmed: 3551820
Org Lett. 2004 Nov 25;6(24):4523-5
pubmed: 15548066
Org Lett. 2012 Aug 17;14(16):4078-81
pubmed: 22857601
J Org Chem. 2015 Feb 6;80(3):1402-13
pubmed: 25569800
Org Lett. 2006 May 25;8(11):2273-6
pubmed: 16706504
Bioorg Med Chem Lett. 2011 Apr 15;21(8):2527-32
pubmed: 21398120
J Org Chem. 1999 Mar 19;64(6):1979-1985
pubmed: 11674292
Beilstein J Org Chem. 2016 Jul 20;12:1551-6
pubmed: 27559405
J Am Chem Soc. 2017 Sep 13;139(36):12398-12401
pubmed: 28832139
Org Biomol Chem. 2007 Mar 21;5(6):873-88
pubmed: 17340001
Bioorg Med Chem Lett. 2016 Feb 15;26(4):1310-3
pubmed: 26786699
Org Lett. 2012 Jul 6;14(13):3296-9
pubmed: 22702411
J Org Chem. 2015 Jan 16;80(2):1082-91
pubmed: 25525945
J Am Chem Soc. 2009 Dec 30;131(51):18240-1
pubmed: 19958032
J Am Chem Soc. 2013 Jul 17;135(28):10338-41
pubmed: 23819732
Chem Commun (Camb). 2008 Sep 21;(35):4177-9
pubmed: 18802521
Chem Pharm Bull (Tokyo). 2009 Dec;57(12):1391-5
pubmed: 19952450
Top Curr Chem. 2015;361:83-136
pubmed: 25467537
J Med Chem. 2014 Oct 9;57(19):8140-51
pubmed: 25192493
Molecules. 2015 Aug 13;20(8):14791-809
pubmed: 26287139
Org Lett. 2005 Jun 9;7(12):2309-11
pubmed: 15932185
Org Biomol Chem. 2019 Aug 7;17(31):7352-7359
pubmed: 31338507
Org Lett. 2017 Feb 3;19(3):476-479
pubmed: 28075602
Eur J Med Chem. 2016 Aug 25;119:197-217
pubmed: 27162124
Chem Asian J. 2011 Sep 5;6(9):2550-9
pubmed: 21780291
Chem Commun (Camb). 2010 Oct 21;46(39):7295-306
pubmed: 20734008
J Am Chem Soc. 2005 Apr 27;127(16):5772-3
pubmed: 15839659
J Org Chem. 2015 Jan 2;80(1):156-64
pubmed: 25422859
Org Lett. 2001 May 31;3(11):1757-60
pubmed: 11405704
Chemistry. 2008;14(28):8603-14
pubmed: 18680117
Org Lett. 2018 Jun 15;20(12):3643-3646
pubmed: 29847943
Bioorg Med Chem Lett. 2011 Mar 1;21(5):1310-4
pubmed: 21315589
Angew Chem Int Ed Engl. 2012 Nov 5;51(45):11376-80
pubmed: 23074015
J Org Chem. 2004 May 28;69(11):3774-81
pubmed: 15153008
Org Lett. 2012 Feb 17;14(4):980-3
pubmed: 22316431
J Org Chem. 2013 Oct 18;78(20):10541-7
pubmed: 24053407
Chem Commun (Camb). 2013 Jan 30;49(9):928-30
pubmed: 23248060
Org Lett. 2018 Sep 21;20(18):5969-5972
pubmed: 30211562
Biochemistry. 2001 Jun 19;40(24):7035-46
pubmed: 11401547
Org Lett. 1999 Oct 7;1(7):1053-5
pubmed: 10825956