Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

Type
Article
Authors
Tong, Guanghu
Zhu, Bo
Lee, Richmond
Yang, Wenguo
Tan, Davin
Yang, Caiyun
Han, Zhiqiang
Yan, Lin
Huang, Kuo-Wei cc
Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-04-26
Online Publication Date
2013-04-26
Print Publication Date
2013-05-17
Permanent link to this record
http://hdl.handle.net/10754/562767

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Abstract
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/jo400496z
Sponsors
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 Chemistry
DOI
10.1021/jo400496z
PubMed ID
23594149
Relations
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
Collections
Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)