Umfang:
Online-Ressource
ISSN:
1099-0690
Inhalt:
Abstract: Described are the studies on the mechanism of the asymmetric Biginelli reaction using proline ester salt catalyst to explain the enantioselectivity of the 3,4‐dihydropyrimidin‐2 (1H)‐one (DHPM) formation. Of the three possible activation methods by the catalyst that could provide asymmetric induction we revealed that the steric environment of the chiral enamine formed by the condensation of β‐keto ester with the catalyst is most responsible for the enantioselectivity. This assumption is supported by experiments with the N‐methylated catalyst, and the combination sets of l‐ or d‐proline ester catalyst with racemic or chiral BINOL‐derived phosphoric acid as counter acid. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
In:
volume:2009
In:
number:23
In:
year:2009
In:
pages:3858-3862
In:
extent:5
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2009, Heft 23 (2009), 3858-3862 (gesamt 5), 1099-0690
Sprache:
Englisch
DOI:
10.1002/ejoc.200900455
URN:
urn:nbn:de:101:1-2023061506505457307632
URL:
https://doi.org/10.1002/ejoc.200900455
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023061506505457307632
URL:
https://d-nb.info/1292782978/34
URL:
https://doi.org/10.1002/ejoc.200900455