54623-66-4Relevant academic research and scientific papers
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.
Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline
Florio, Saverio,Capriati, Vito,Luisi, Renzo
, p. 5295 - 5298 (2007/10/03)
Boron and titanium azaenolates 2 and 4, generated at 0°C and -100°C, respectively, from the optically active chloromethyloxazoline 1, have been found to couple with aliphatic ketones in a highly diastereoselective fashion ending up with the formation of optically active oxazolinyl oxiranes 3. Less stereoselective was the reaction with aromatic ketones. (C) 2000 Elsevier Science Ltd.
Synthesis of optically active 2-chloromethyl-2-oxazolines by the ortho- ester condensation method using triethyl orthochloroacetate
Kamata, Kazuyuki,Sato, Hideki,Takagi, Emi,Agata, Isao,Meyers
, p. 373 - 378 (2007/10/03)
A set of optically active 2-chloromethyl-2-oxazolines was synthesized by condensation of optically active 2-amino alcohols with triethyl orthochloroacetate which was prepared conveniently from triethyl orthoacetate by chlorination using tert-butyl hypochlorite.
