355410-80-9Relevant academic research and scientific papers
Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes
Capriati, Vito,Florio, Saverio,Luisi, Renzo
, p. 2035 - 2039 (2007/10/03)
The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.
On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds
Florio, Saverio,Capriati, Vito,Luisi, Renzo,Abbotto, Alessandro,Pippel, Daniel J
, p. 6775 - 6786 (2007/10/03)
Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to furnish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported.
