Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2013-04-26
Print Publication Date2013-05-17
Permanent link to this recordhttp://hdl.handle.net/10754/562767
MetadataShow full item record
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.
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
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 (ACS)
JournalJournal of Organic Chemistry
RelationsIs Supplemented By:
- Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates.
- Authors: Yang W, Tan D, Li L, Han Z, Yan L, Huang KW, Tan CH, Jiang Z
- Issue date: 2012 Aug 3
- Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.
- Authors: Cui HL, Huang JR, Lei J, Wang ZF, Chen S, Wu L, Chen YC
- Issue date: 2010 Feb 19
- Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates.
- Authors: Jiang K, Peng J, Cui HL, Chen YC
- Issue date: 2009 Jul 14
- An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles.
- Authors: Wang QL, Peng L, Wang FY, Zhang ML, Jia LN, Tian F, Xu XY, Wang LX
- Issue date: 2013 Oct 21
- Asymmetric organocatalytic allylic alkylation of Reissert compounds: a facile access to chiral 1,1-disubstituted 1,2-dihydroisoquinolines.
- Authors: Qin TY, Liao WW, Zhang YJ, Zhang SX
- Issue date: 2013 Feb 14