In:
European Journal of Organic Chemistry, Wiley, Vol. 2017, No. 26 ( 2017-07-17), p. 3874-3885
Kurzfassung:
Enantioselective crossed aldol reactions of isatin derivatives and acetaldehyde have been developed with a series of simple diamino alcohol catalysts to afford 3‐substituted 3‐hydroxyindolin‐2‐ones in high chemical yields (up to 95 %) and optical purities (up to 92 % ee ). The synthetic potential of the present protocol has been demonstrated by concise, enantioselective, protecting‐group‐free, and transition metal‐free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC‐1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible transition states.
Materialart:
Online-Ressource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2017.26
DOI:
10.1002/ejoc.201700399
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2017
ZDB Id:
1475010-7
