95207-39-9Relevant academic research and scientific papers
Regiospecific Conversion of Oxiranes, Oxetanes, and Lactones into Difunctional Nitrogen Compounds via Aminosilanes and Aminostannanes
Papini, Annamaria,Ricci, Alfredo,Taddei, Maurizio,Seconi, Giancarlo,Dembech, Pasquale
, p. 2261 - 2266 (2007/10/02)
The insertion reactions of diethylaminotrimethylsilane (TMSDEA) and diethylaminotrimethylstannane (TMSnDEA) into oxirane, oxetane, and lactone rings are reported.Regioisomerically pure β- and γ-amino alcohols were obtained, with AlCl3 or Et2AlCl catalysis, from monoalkyloxiranes and monoalkyl- and aryl-oxetanes respectively, whereas, in the majority of cases, reactions involving polysubstituted oxiranes resulted in a loss of regoiselectivity.Ring-opening reactions of the lactone rings with TMSDEA led, on the other hand, to β-amino acids or to ω-hydroxyamides depending upon the ring size.With TMSnDEA, spontaneous ring cleavage of the alkyloxiranes and β-propiolactone occurred with reversed regioselectivity, while the oxetanes and γ- and δ-lactones were opened with the same regiochemistry as that found with TMSDEA for the same ring systems.
