RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2015; 26(18): 2541-2546
DOI: 10.1055/s-0035-1560636
DOI: 10.1055/s-0035-1560636
letter
Catalytic Enantioselective Synthesis of Chiral 3-Amino-2-oxindoles by a Mannich Approach
Weitere Informationen
Publikationsverlauf
Received: 17. Juni 2015
Accepted after revision: 31. August 2015
Publikationsdatum:
29. September 2015 (online)


Abstract
A catalytic enantioselective Mannich-type reaction of a cyclohexanone-derived alkenyl trichloroacetate with isatin imines was achieved using an (S)-BINOL-derived chiral tin dibromide possessing a 4-tert-butylphenyl group at 3- and 3′-positions as the chiral precatalyst in the presence of sodium methoxide, sodium iodide, and methanol. Optically active 3-alkylated 3-amino-2-oxindoles having up to 90% enantiomeric excess were diastereoselectively obtained in high yields under the influence of the in situ generated chiral tin iodide methoxide.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560636.
- Supporting Information