93684-44-7Relevant academic research and scientific papers
Convenient one-pot synthesis of 2-oxazolines from carboxylic acids
Hioki, Kazuhito,Takechi, Yumiko,Kimura, Noriyo,Tanaka, Hiroyuki,Kunishima, Munetaka
experimental part, p. 1735 - 1737 (2009/10/10)
Simple one-pot methods for preparation of 2-oxazolines have been developed using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Treatment of a mixture of carboxylic acids and 2-haloethylammonium salts with DMT-MM in methanol
CONDENSATION REACTION BY METAL CATALYST
-
Page/Page column 24-25, (2008/12/07)
The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein R1 represents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R3, R4, R5 and R6 may be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R3, R4, R5 and R6 may bond to each other to form a ring; and Z1 represents an oxygen atom, a sulfur atom or a selenium atom; comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1): ????????R1CO2R2?????(1) wherein R1 is as defined above; R2 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group; and R1 and R2 may bond to each other to form a ring; with an aminochalcogenide represented by the general formula (2): wherein R3, R4, R5, R6 and Z1 are as defined above; in the presence of a compound containing a group 12 metal element in the periodic table.
Direct conversion of esters, lactones, and carboxylic acids to oxazolines catalyzed by a tetranuclear zinc cluster
Ohshima, Takashi,Iwasaki, Takanori,Mashima, Kazushi
, p. 2711 - 2713 (2008/09/21)
The tetranuclear zinc cluster Zn4(OCOCF3) 6O catalyzes the direct conversion of esters, lactones, and carboxylic acids to oxazolines with remarkable chemoselectivity. The Royal Society of Chemistry 2006.
Asymmetric Induction in the Claisen Rearrangement of N-Allylketene N,O-Acetals
Kurth, Mark J.,Decker, Owen H. W.,Hope, Hakon,Yanuck, Michael D.
, p. 443 - 448 (2007/10/02)
Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 1 is described.Diastereoselection noted for rearrangement 1->2 ranges from 84percent to 96percent and is a consequence of complete (Z)-N,O-acetal olefin selectivity in 1, high Cα-si-face selectivity in the rearrangement of 1 to 2, and the absence of Cα epimerization in oxazoline 2.Experiments which establish the steric bulk of the C4 appendage as a particularly important variable are also reported.Acid-catalyzed hydrolysis of rearranged oxazoline 2 completes an efficient, enantioselective synthesis of 2-substituted pent-4-enoic acid 4 and regenerates for recycling the chiral auxiliary reagent 3, initially prepared from inexpensive α-amino acids.
