α-(Aminomethyl)acrylates as acceptors in radical-polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping.
radical–polar crossover
tandem reactions
tert-butanesulfinamide
zinc radical transfer
β-amino acids
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2023
2023
Historique:
received:
27
07
2023
accepted:
12
09
2023
medline:
28
9
2023
pubmed:
28
9
2023
entrez:
28
9
2023
Statut:
epublish
Résumé
We demonstrate that α-(aminomethyl)acrylates are suitable acceptors for 1,4-additions of dialkylzincs in aerobic conditions. The air-promoted radical-polar crossover process involves the 1,4-addition of an alkyl radical followed by homolytic substitution at the zinc atom of dialkylzinc. Coordination of the nitrogen atom to zinc enables this S
Identifiants
pubmed: 37767333
doi: 10.3762/bjoc.19.103
pmc: PMC10520473
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1443-1451Informations de copyright
Copyright © 2023, Palillero-Cisneros et al.
Références
Biopolymers. 2004;76(3):206-43
pubmed: 15148683
Angew Chem Int Ed Engl. 2003 Sep 5;42(34):4043-6
pubmed: 12973764
Chemistry. 2006 Aug 25;12(25):6506-13
pubmed: 16789032
J Org Chem. 2012 Jul 6;77(13):5775-80
pubmed: 22667329
Acc Chem Res. 2008 Oct;41(10):1366-75
pubmed: 18578513
Org Lett. 2005 Jun 23;7(13):2571-3
pubmed: 15957893
Chem Asian J. 2013 Sep;8(9):2167-74
pubmed: 23776190
Chemistry. 2012 Mar 12;18(11):3241-7
pubmed: 22328494
J Org Chem. 2016 May 6;81(9):3809-17
pubmed: 27080088
Proc Natl Acad Sci U S A. 2007 Oct 23;104(43):16787-92
pubmed: 17942689
Chem Rev. 2001 Oct;101(10):3219-32
pubmed: 11710070
Org Lett. 2016 Dec 16;18(24):6372-6375
pubmed: 27978670
Angew Chem Int Ed Engl. 2004 Feb 27;43(10):1235-8
pubmed: 14991786