Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage
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 Date2012-02-08
Print Publication Date2012-04
Permanent link to this recordhttp://hdl.handle.net/10754/562090
MetadataShow full item record
AbstractThrough the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
CitationYang, W., Tan, D., Lee, R., Li, L., Pan, Y., Huang, K.-W., … Jiang, Z. (2012). Catalytic Diastereoselective Tandem Conjugate Addition-Elimination Reaction of Morita-Baylis-Hillman C Adducts by CC Bond Cleavage. Chemistry - An Asian Journal, 7(4), 771–777. doi:10.1002/asia.201100863
SponsorsFinancial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.
JournalChemistry - An Asian Journal
- 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
- Highly enantio- and diastereoselective synthesis of β-methyl-γ-monofluoromethyl-substituted alcohols.
- Authors: Yang W, Wei X, Pan Y, Lee R, Zhu B, Liu H, Yan L, Huang KW, Jiang Z, Tan CH
- Issue date: 2011 Jul 11
- Formation of carbocycles by intramolecular conjugate displacement: scope and mechanistic insights.
- Authors: Wang L, Prabhudas B, Clive DL
- Issue date: 2009 Apr 29
- 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
- Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones.
- Authors: Tong G, Zhu B, Lee R, Yang W, Tan D, Yang C, Han Z, Yan L, Huang KW, Jiang Z
- Issue date: 2013 May 17