The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: Access to chiral γ-Butenolides and glycerol derivatives
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
MetadataShow full item record
AbstractTwice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
SponsorsWe thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.
Is Supplemented ByLuo, J., Wang, H., Han, X., Xu, L.-W., Kwiatkowski, J., Huang, K.-W., & Lu, Y. (2011). CCDC 803555: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvz543
- Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes.
- Authors: Pansare SV, Paul EK
- Issue date: 2011 Jan 21
- Asymmetric direct vinylogous aldol reaction of unactivated gamma-butenolide to aldehydes.
- Authors: Yang Y, Zheng K, Zhao J, Shi J, Lin L, Liu X, Feng X
- Issue date: 2010 Aug 6
- Novel synthons from mucochloric acid: the first use of alpha,beta-dichloro-gamma-butenolides and gamma-butyrolactams for direct vinylogous aldol addition.
- Authors: Das Sarma K, Zhang J, Curran TT
- Issue date: 2007 Apr 27
- Catalytic, asymmetric synthesis of phosphonic γ-(hydroxyalkyl)butenolides with contiguous quaternary and tertiary stereogenic centers.
- Authors: Frings M, Thomé I, Schiffers I, Pan F, Bolm C
- Issue date: 2014 Feb 3
- Catalytic asymmetric synthesis of γ-butenolides by direct vinylogous reactions.
- Authors: Yan L, Wu X, Liu H, Xie L, Jiang Z
- Issue date: 2013 May 1