In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 9, No. 13 ( 2022), p. 3446-3451
Abstract:
The first highly enantioselective asymmetric vinylogous Michael addition of α,α-dicyanoalkenes with 3-alkenyl-oxindoles catalyzed by chiral-at-metal complexes to deliver 3,3′-disubstituted oxindole bearing an all-carbon quaternary stereocenter has been developed. In the presence of 1.0 mol% of chiral Rh( iii ) complex, corresponding adducts were obtained in 21–98% yields with 80–97% ee. Remarkably, this protocol exhibited excellent advantages in terms of enantioselectivity, given the fact that as low as 0.05 mol% of chiral Rh( iii ) complex could promote the title reaction on a gram scale to afford the desired product with excellent enantiomer excess values. In addition, the utility of this approach was verified by the formal synthesis of sulfur-containing heterocyclic compounds.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
