Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones
Type
ArticleAuthors
Tong, GuanghuZhu, Bo
Lee, Richmond
Yang, Wenguo
Tan, Davin
Yang, Caiyun
Han, Zhiqiang
Yan, Lin
Huang, Kuo-Wei

Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-04-26Online Publication Date
2013-04-26Print Publication Date
2013-05-17Permanent link to this record
http://hdl.handle.net/10754/562767
Metadata
Show full item recordAbstract
The 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.Citation
Tong, 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/jo400496zSponsors
Financial 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.Publisher
American Chemical Society (ACS)Journal
The Journal of Organic ChemistryPubMed ID
23594149Relations
Is Supplemented By:- [Dataset]
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: 10.5517/cczjcnh HANDLE: 10754/624757
ae974a485f413a2113503eed53cd6c53
10.1021/jo400496z
Scopus Count
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