The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding

Handle URI:
http://hdl.handle.net/10754/562513
Title:
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, Richmond; Zhong, Fangrui; Zheng, Bin; Meng, Yuezhong; Lu, Yixin; Huang, Kuo-Wei ( 0000-0003-1900-2658 )
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. © 2013 The Royal Society of Chemistry.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Organic & Biomolecular Chemistry
Issue Date:
2013
DOI:
10.1039/c3ob40144h
PubMed ID:
23774825
Type:
Article
ISSN:
14770520
Sponsors:
We 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.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLee, Richmonden
dc.contributor.authorZhong, Fangruien
dc.contributor.authorZheng, Binen
dc.contributor.authorMeng, Yuezhongen
dc.contributor.authorLu, Yixinen
dc.contributor.authorHuang, Kuo-Weien
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)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalOrganic & Biomolecular Chemistryen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
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, Chinaen
kaust.authorLee, Richmonden
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien
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