Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
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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.
SponsorsFinancial 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.
PublisherAmerican Chemical Society
JournalJournal of Organic Chemistry
Is Supplemented ByTong, 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
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