Chemoselective reduction model of aliphatic esters with sodium borohydride
Lue Xiao-Jie1,2; Jiang Ju-Xing1,2; Ren Jie1; Zhu Hua-Jie1
AbstractSodium borohydride has been widely used in different organic reductions due to its moderate chemical activity. The reductions of ester with sodium borohydride could produce various alcohols as intermediates for further reactions. The esters with different alkyl substituents are used as the models in sodium borohydride reductions, and on-set temperatures, half-life periods and transition state(TS) energies were obtained experimentally. Some of the TS energetics were computed using B3LYP/6-31 + + G (d, p)//HF/6-31G (d,p) method. The differences of on-set temperatures among these esters were substantial and some observed selectivities were obtained when the aliphatic substituents changed from Me, Et, n-Pr to n-Bu. Odd-even carbon effect, which was first mentioned in our previous report in enantioselective additions of diethylzine to benzaldehyde, was observed again in the reductions. Traditionally, organic theory uses the size of the substitutents to explain the reaction TS energy order. However, the traditional theory can not be used to explain the observed odd-even carbon effect. The reason for this effect happened in different reactions is still unknown. Furthermore, the effect of solvent in the reductions was investigated primarily.
KeywordAliphatic Esters Chemoselective Reduction Transition State Energy Half-life Period Odd-even Carbon Effect
Subject AreaChemistry ; Multidisciplinary
Indexed BySCI
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000254265100022
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Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Affiliation1.Chinese Acad Sci, Organ Synth & Nat Prod Lab, State Key Lab Phytochem & Plant Resources W China, Kunming Inst Bot, Kunming 650204, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
Recommended Citation
GB/T 7714
Lue Xiao-Jie,Jiang Ju-Xing,Ren Jie,et al. Chemoselective reduction model of aliphatic esters with sodium borohydride[J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,2008,29(3):537-541.
APA Lue Xiao-Jie,Jiang Ju-Xing,Ren Jie,&Zhu Hua-Jie.(2008).Chemoselective reduction model of aliphatic esters with sodium borohydride.CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,29(3),537-541.
MLA Lue Xiao-Jie,et al."Chemoselective reduction model of aliphatic esters with sodium borohydride".CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE 29.3(2008):537-541.
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