ICCAS OpenIR
Efficient Baylis-Hillman reactions of cyclic enones in methanol as catalyzed by methoxide anion
Luo, SZ; Mi, XL; Xu, H; Wang, PG; Cheng, JP
2004-11-26
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume69Issue:24Pages:8413-8422
AbstractThe Baylis-Hillman reactions of cyclic enones with a variety of aldehydes were investigated. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was found to be a viable catalyst in promoting the reactions of sterically retarded substrates in methanol. The reactions showed clear solvent dependence and only occurred in hydroxylic solvents, especially in methanol. Further consideration on the steric character of DBU and its high basicity jointly with other experimental observations suggests that the methoxide anion should be the "true" Baylis-Hillman catalyst. This has been confirmed by the effectiveness of similar reactions directly employing methoxide as the catalyst. The reaction pathways of this type of catalysis are proposed to depend on the choice of substrates. Supporting experimental observations were demonstrated and discussed in relation to mechanistic considerations. This study also reveals that both DBU and sodium methoxide can be successfully applied as effective catalysts in methanol to promote the Baylis-Hillman reactions for a range of cyclic enones including cyclopent-2-enones, cyclohex-2-enones, gamma-pyrone, and 1-benzopyran-4(4H)-ones.
DOI10.1021/jo0491760
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000225341300032
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:66[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/82098
Collection中国科学院化学研究所
Corresponding AuthorCheng, JP
Affiliation1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
2.Nankai Univ, Dept Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
3.Shandong Univ, Sch Life Sci, State Key Lab Microbial Technol, Jinan 250100, Peoples R China
Recommended Citation
GB/T 7714
Luo, SZ,Mi, XL,Xu, H,et al. Efficient Baylis-Hillman reactions of cyclic enones in methanol as catalyzed by methoxide anion[J]. JOURNAL OF ORGANIC CHEMISTRY,2004,69(24):8413-8422.
APA Luo, SZ,Mi, XL,Xu, H,Wang, PG,&Cheng, JP.(2004).Efficient Baylis-Hillman reactions of cyclic enones in methanol as catalyzed by methoxide anion.JOURNAL OF ORGANIC CHEMISTRY,69(24),8413-8422.
MLA Luo, SZ,et al."Efficient Baylis-Hillman reactions of cyclic enones in methanol as catalyzed by methoxide anion".JOURNAL OF ORGANIC CHEMISTRY 69.24(2004):8413-8422.
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