77086-43-2Relevant academic research and scientific papers
Highly Effective Catalysts for the Conjugate Addition of Silyl Ketene Acetals to Enones (Mukaiyama-Micael Reaction)
Berl, Valerie,Helmchen, Guenter,Preston, Stephanie
, p. 233 - 236 (1994)
Conjugate additions of O-silylated ketene acetals to simple enones have been reported to proceed without a catalyst if acetonitrile is used as solvent.Inability to repeat this procedure led to the discovery that an as yet unknown species formed from P4O10
Spontaneous aldol and Michael additions of simple enoxytrimethylsilanes in DMSO
Génisson, Yves,Gorrichon, Liliane
, p. 4881 - 4884 (2007/10/03)
Activation of simple trimethylsilyl ketene acetals by dipolar aprotic solvents has been evidenced, allowing efficient solvent assisted aldol and Michael additions under extremely simple, mild and metal free conditions. (C) 2000 Elsevier Science Ltd.
Mukaiyama aldol and Michael reactions catalyzed by lanthanide iodides
Giuseppone, Nicolas,Van De Weghe, Pierre V.,Mellah, Mohamed,Collin, Jacqueline
, p. 13129 - 13148 (2007/10/03)
Samarium diiodide is an efficient catalyst precursor which allows the formation of condensation products between various carbonyl compounds and ketene silyl acetals or enoxysilanes. With α,β-unsaturated carbonyl compounds, 1,2- or 1,4-additions are observed according to the structure of the substrate. α,β-Unsaturated ketones yield to enoxysilanes by selective Michael additions. Aldol products are isolated as silyl ethers. The mechanisms of the reactions are discussed.
Keten Silyl Acetal Chemistry; Simple Synthesis of Methyl Jasmonate and Related Compounds by Utilising Keten Methyl Dimethyl-t-butylsilyl Acetal
Kita, Yasuyuki,Segawa, Jun,Haruta, Jun-ichi,Yasuda, Hitoshi,Tamura, Yasumitsu
, p. 1099 - 1104 (2007/10/02)
Conjugate addition of keten silyl acetals to α,β-unsaturated carbonyl compounds in acetonitrile gave a quantitative yield of the corresponding methyl (3-trialkylsiloxyalk-2-enyl)acetates; subsequent site-specific electrophilic substitution yielded the corresponding 2-substituted 3-(alkoxycarbonylmethyl)alkanones.These novel addition and sequential alkylation reactions could be applied to a simple synthesis of methyl jasmonate, methyl didehydrojasmonate, and methyl dihydrojasmonate.
O-silylated ketene acetal chemistry; β-(alkoxycarbonyl)methyl O-silyl enolates, useful synthons for α-substituted-β-(alkoxycarbonyl)methylalkanones
Kita,Segawa,Haruta,Fujii,Tamura
, p. 3779 - 3782 (2007/10/02)
Conjugate addition of O-silylated ketene acetals 2 to α,β-unsaturated carbonyl compounds 1 in acetonitrile gave quantitative yields of the corresponding β-(alkoxycarbonyl)methyl O-silyl enolates 4. Site specific electrophilic substitutions of 4 yielded th
