Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Type
Article
Authors
Yang, Wenguo
Tan, Davin
Lee, Richmond
Li, Lixin
Pan, Yuanhang
Huang, Kuo-Wei cc
Tan, Choonhong
Jiang, Zhiyong
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Date
2012-02-08
Online Publication Date
2012-02-08
Print Publication Date
2012-04
Permanent link to this record
http://hdl.handle.net/10754/562090

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Abstract
Through 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.
Sponsors
Financial 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.
Publisher
Wiley
Journal
Chemistry - An Asian Journal
DOI
10.1002/asia.201100863
PubMed ID
22318922
Collections
Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)