Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.
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:
20
10
2021
medline:
27
1
2022
entrez:
19
10
2021
Statut:
ppublish
Résumé
We present highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates. "Arming" the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity in these reactions. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The scalability of the oxidative cyclization was demonstrated, and the product cyclophosphoramidates were shown to be valuable synthons, including for tether removal. With chiral alkenyl precursors, enantiopure cyclic phosphoramidates were formed.
Identifiants
pubmed: 34665630
doi: 10.1021/acs.joc.1c01483
pmc: PMC10119688
mid: NIHMS1891742
doi:
Substances chimiques
Amides
0
Phosphoric Acids
0
phosphoramidic acid
9Q189608GB
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
14732-14758Subventions
Organisme : NIGMS NIH HHS
ID : P20 GM113117
Pays : United States
Références
Org Lett. 2010 Mar 19;12(6):1248-51
pubmed: 20184343
Nat Prod Rep. 2019 Jan 1;36(1):174-219
pubmed: 29923586
J Am Chem Soc. 2019 Jun 19;141(24):9712-9718
pubmed: 31136168
J Org Chem. 2003 Feb 7;68(3):1012-7
pubmed: 12558429
Org Lett. 2020 Feb 7;22(3):896-901
pubmed: 31927967
Chemistry. 2012 Nov 19;18(47):15151-7
pubmed: 23033176
Angew Chem Int Ed Engl. 2013 Nov 4;52(45):11867-70
pubmed: 24105928
Chem Rev. 2010 Feb 10;110(2):1147-69
pubmed: 20078038
J Am Chem Soc. 2006 Mar 15;128(10):3130-1
pubmed: 16522078
Org Lett. 2017 Jan 20;19(2):316-319
pubmed: 28068102
Isr J Chem. 2020 Mar;60(3-4):259-267
pubmed: 33664525
Org Lett. 2009 Dec 17;11(24):5626-8
pubmed: 19905004
Org Lett. 2017 Jul 7;19(13):3592-3595
pubmed: 28636402
J Org Chem. 2004 Aug 20;69(17):5627-30
pubmed: 15307732
Inorg Chem. 2007 Mar 19;46(6):1910-23
pubmed: 17348722
Angew Chem Int Ed Engl. 2003 Jun 30;42(25):2892-5
pubmed: 12833351
Org Biomol Chem. 2016 Jun 28;14(24):5440-53
pubmed: 27120353
Chem Commun (Camb). 2013 May 21;49(41):4619-21
pubmed: 23589822
Org Lett. 2018 Apr 20;20(8):2386-2390
pubmed: 29595983
Synthesis (Stuttg). 2018 Dec;50(24):4699-4714
pubmed: 31105348
J Am Chem Soc. 2016 May 11;138(18):5805-8
pubmed: 27093112
Chem Rev. 2017 Jul 12;117(13):8754-8786
pubmed: 28697604
Angew Chem Int Ed Engl. 2010 Jul 26;49(32):5529-32
pubmed: 20583013
J Am Chem Soc. 2017 Aug 9;139(31):10657-10660
pubmed: 28738150
J Am Chem Soc. 2018 Jun 20;140(24):7587-7597
pubmed: 29804449
Angew Chem Int Ed Engl. 2004 Jun 28;43(26):3368-98
pubmed: 15221826
Angew Chem Int Ed Engl. 2009;48(28):5094-115
pubmed: 19557755
Chem Soc Rev. 2009 Nov;38(11):3242-72
pubmed: 19847354
Org Lett. 2020 Nov 6;22(21):8665-8669
pubmed: 33095992
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
Chem Sci. 2020 Jul 21;11(31):8073-8088
pubmed: 34123081
J Am Chem Soc. 2015 Jul 29;137(29):9226-9
pubmed: 26166022
Chem Commun (Camb). 2011 Mar 21;47(11):3043-56
pubmed: 21246123