Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

Handle URI:
http://hdl.handle.net/10754/562269
Title:
Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates
Authors:
Yang, Wenguo; Tan, Davin; Li, Lixin; Han, Zhiqiang; Yan, Lin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Choonhong; Jiang, Zhiyong
Abstract:
The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
American Chemical Society (ACS)
Journal:
The Journal of Organic Chemistry
Issue Date:
3-Aug-2012
DOI:
10.1021/jo3012539
PubMed ID:
22816444
Type:
Article
ISSN:
00223263
Sponsors:
Financial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.
Is Supplemented By:
Yang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K.-W., … Jiang, Z. (2013). CCDC 874217: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccybpkh; DOI:10.5517/ccybpkh; HANDLE:http://hdl.handle.net/10754/624688
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorYang, Wenguoen
dc.contributor.authorTan, Davinen
dc.contributor.authorLi, Lixinen
dc.contributor.authorHan, Zhiqiangen
dc.contributor.authorYan, Linen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Choonhongen
dc.contributor.authorJiang, Zhiyongen
dc.date.accessioned2015-08-03T09:58:46Zen
dc.date.available2015-08-03T09:58:46Zen
dc.date.issued2012-08-03en
dc.identifier.issn00223263en
dc.identifier.pmid22816444en
dc.identifier.doi10.1021/jo3012539en
dc.identifier.urihttp://hdl.handle.net/10754/562269en
dc.description.abstractThe asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.en
dc.description.sponsorshipFinancial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleDirect asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonatesen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalThe Journal of Organic Chemistryen
dc.contributor.institutionInstitute of Chemical Biology, Henan University, Kaifeng, Henan, 475004, Chinaen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, Chinaen
dc.contributor.institutionDivision of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singaporeen
kaust.authorTan, Davinen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByYang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K.-W., … Jiang, Z. (2013). CCDC 874217: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccybpkhen
dc.relation.isSupplementedByDOI:10.5517/ccybpkhen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624688en

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