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dc.contributor.authorLee, Richmond*
dc.contributor.authorZhong, Fangrui*
dc.contributor.authorZheng, Bin*
dc.contributor.authorMeng, Yuezhong*
dc.contributor.authorLu, Yixin*
dc.contributor.authorHuang, Kuo-Wei*
dc.date.accessioned2015-08-03T10:40:54Zen
dc.date.available2015-08-03T10:40:54Zen
dc.date.issued2013en
dc.identifier.issn14770520en
dc.identifier.pmid23774825en
dc.identifier.doi10.1039/c3ob40144hen
dc.identifier.urihttp://hdl.handle.net/10754/562513en
dc.description.abstractl-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. © 2013 The Royal Society of Chemistry.en
dc.description.sponsorshipWe are grateful for the generous financial support from King Abdullah University of Science and Technology to K.-W.H. and from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-494-112) to Y. L.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleThe origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bondingen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)*
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division*
dc.contributor.departmentChemical Science Program*
dc.contributor.departmentHCL*
dc.identifier.journalOrganic & Biomolecular Chemistryen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore*
dc.contributor.institutionKey Laboratory of Low-carbon Chemistry and Energy Conservation of Guangdong Province, State Key Laboratory of Optoelectronic Materials and Technologies, Sun Yat-sen University, Guangzhou 510275, China*
kaust.personLee, Richmond*
kaust.personZheng, Bin*
kaust.personHuang, Kuo-Wei*


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