title: The origin of enantioselectivity in the L-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: effects of the intramolecular hydrogen bonding.
abstract: L-Threonine-derived phosphine-sulfonamide 4 was identified as the most efficient catalyst to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions, affording the desired aza-MBH adducts with excellent enantioselectivities. Density functional theory (DFT) studies were carried out to elucidate the origin of the observed enantioselectivity. The importance of the intramolecular N-H···O hydrogen-bonding interaction between the sulfonamide and enolate groups was identified to be crucial in inducing a high degree of stereochemical control in both the enolate addition to imine and the subsequent proton transfer step, affording aza-MBH reactions with excellent enantioselectivity.
authors.affiliation: Division of Physical Sciences and Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia.
authors.forename: Richmond
authors.initials: R
authors.lastname: Lee
authors.forename: Fangrui
authors.initials: F
authors.lastname: Zhong
authors.forename: Bin
authors.initials: B
authors.lastname: Zheng
authors.forename: Yuezhong
authors.initials: Y
authors.lastname: Meng
authors.forename: Yixin
authors.initials: Y
authors.lastname: Lu
authors.forename: Kuo-Wei
authors.initials: KW
authors.lastname: Huang
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006860:Hydrogen Bonding; D010720:Phosphines / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D010720:Phosphines; D013449:Sulfonamides; D013912:Threonine; C044646:phosphine