L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Permanent link to this recordhttp://hdl.handle.net/10754/561734
MetadataShow full item record
AbstractA series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities. © 2011 American Chemical Society.
SponsorsWe are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) to Y.L. and from King Abdullah University of Science and Technology to K.-W.H.
PublisherAmerican Chemical Society (ACS)
- The origin of enantioselectivity in the L-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: effects of the intramolecular hydrogen bonding.
- Authors: Lee R, Zhong F, Zheng B, Meng Y, Lu Y, Huang KW
- Issue date: 2013 Aug 7
- Enantioselective Morita-Baylis-Hillman reaction promoted by L-threonine-derived phosphine-thiourea catalysts.
- Authors: Han X, Wang Y, Zhong F, Lu Y
- Issue date: 2011 Oct 7
- Base-accelerated enantioselective substitution of Morita-Baylis-Hillman carbonates with dialkyl phosphine oxides.
- Authors: Sun W, Hong L, Liu C, Wang R
- Issue date: 2010 Sep 3
- Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations.
- Authors: Wang T, Han X, Zhong F, Yao W, Lu Y
- Issue date: 2016 Jul 19
- Highly enantioselective [3+2] annulation of Morita-Baylis-Hillman adducts mediated by L-threonine-derived phosphines: synthesis of 3-spirocyclopentene-2-oxindoles having two contiguous quaternary centers.
- Authors: Zhong F, Han X, Wang Y, Lu Y
- Issue date: 2011 Aug 16