Show simple item record

dc.contributor.authorTong, Guanghu
dc.contributor.authorZhu, Bo
dc.contributor.authorLee, Richmond
dc.contributor.authorYang, Wenguo
dc.contributor.authorTan, Davin
dc.contributor.authorYang, Caiyun
dc.contributor.authorHan, Zhiqiang
dc.contributor.authorYan, Lin
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorJiang, Zhiyong
dc.date.accessioned2015-08-03T11:05:00Z
dc.date.available2015-08-03T11:05:00Z
dc.date.issued2013-04-26
dc.identifier.citationTong, G., Zhu, B., Lee, R., Yang, W., Tan, D., Yang, C., … Jiang, Z. (2013). Highly Enantio- and Diastereoselective Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Allyl Ketones. The Journal of Organic Chemistry, 78(10), 5067–5072. doi:10.1021/jo400496z
dc.identifier.issn00223263
dc.identifier.pmid23594149
dc.identifier.doi10.1021/jo400496z
dc.identifier.urihttp://hdl.handle.net/10754/562767
dc.description.abstractThe asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.
dc.description.sponsorshipFinancial support from the National Natural Science Foundation of China (No. 21072044, 21202034), the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938), Excellent Youth Foundation of Henan Scientific Committee (114100510003) and Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) are greatly appreciated. We also thank Professor Choon-Hong Tan (Nanyang Technological University, Singapore) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics, PR China) for their generous help in high resolution mass spectrum analysis.
dc.publisherAmerican Chemical Society (ACS)
dc.titleHighly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalJournal of Organic Chemistry
dc.contributor.institutionInstitute of Chemical Biology, Henan University, Kaifeng, Henan, 475004, China
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, China
kaust.personLee, Richmond
kaust.personTan, Davin
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/cczjcnh
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Tong, G., Zhu, B., Lee, R., Yang, W., Tan, D., Yang, C., … Jiang, Z. (2013). CCDC 909467: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczjcnh. DOI: <a href="https://doi.org/10.5517/cczjcnh">10.5517/cczjcnh</a> HANDLE: <a href="http://hdl.handle.net/10754/624757">10754/624757</a></li></ul>
dc.date.published-online2013-04-26
dc.date.published-print2013-05-17


This item appears in the following Collection(s)

Show simple item record