About: ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL)

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About: ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL) Goto Sponge NotDistinct Permalink

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Description	(Z)-1,3-diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-on (1) is quite easily accessible via ferricyanide oxidation of 2,4,6-triphenyl-1-(pyridin-2-yl)pyridinium perchlorate.Restricted rotation around carbon - carbon bond connecting the heteroaromatic ring with the propenone chain causes an axial chirality of compound (1). This was proved by 1H NMR measurement in the presence of a chiral shift reagent and by diastereoselective borohydride reduction of the prochiral carbonyl group some time ago. We wanted to determine the regioselectivity and diastereoselectivity of organometallic addition reaction to enone (1). Thus we carried out a series of experiments with selected organolithium as well as Grignard reagents in various solvents and obtained 1,2-addition product exclusively in all cases. (Z)-1,3-diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-on (1) is quite easily accessible via ferricyanide oxidation of 2,4,6-triphenyl-1-(pyridin-2-yl)pyridinium perchlorate.Restricted rotation around carbon - carbon bond connecting the heteroaromatic ring with the propenone chain causes an axial chirality of compound (1). This was proved by 1H NMR measurement in the presence of a chiral shift reagent and by diastereoselective borohydride reduction of the prochiral carbonyl group some time ago. We wanted to determine the regioselectivity and diastereoselectivity of organometallic addition reaction to enone (1). Thus we carried out a series of experiments with selected organolithium as well as Grignard reagents in various solvents and obtained 1,2-addition product exclusively in all cases. (en)
Title	ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL) ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL) (en)
skos:prefLabel	ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL) ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL (Z)-1,3-DIPHENYL-3-(2-PHENYLIMIDAZO[1,2-a]PYRIDIN-3-YL) (en)
skos:notation	RIV/60461373:22310/03:00008259!RIV/2004/MSM/223104/N
http://linked.open.../vavai/riv/strany	157
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM 223100001)
http://linked.open...vai/riv/dodaniDat	2004
http://linked.open...aciTvurceVysledku	Böhm, Stanislav Rybáček, Jiří
http://linked.open.../riv/druhVysledku	D - Článek ve sborníku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	597480
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/03:00008259
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	(Z)-1,3-diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-on; organometallic reagents; addition (en)
http://linked.open.../riv/klicoveSlovo	addition (Z)-1 2-a]pyridin-3-yl)prop-2-en-1-on 3-diphenyl-3-(2-phenylimidazo[1 organometallic reagents
http://linked.open...ontrolniKodProRIV	[505CBBF7EA21]
http://linked.open...v/mistoKonaniAkce	Wien
http://linked.open...i/riv/mistoVydani	Wien
http://linked.open...i/riv/nazevZdroje	10th Blue Danube Symposium on Heterocyclic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	2 (xsd:int)
http://linked.open...ocetUcastnikuAkce	0 (xsd:int)
http://linked.open...nichUcastnikuAkce	0 (xsd:int)
http://linked.open...UplatneniVysledku	2003
http://linked.open...iv/tvurceVysledku	Böhm, Stanislav Rybáček, Jiří
http://linked.open...vavai/riv/typAkce	EUR - Evropská
http://linked.open.../riv/zahajeniAkce	2003-09-03 (xsd:date)
http://linked.open...n/vavai/riv/zamer	http://linked.opendata.cz/resource/domain/vavai/zamer/MSM%20223100001
number of pages	1 (xsd:int)
http://purl.org/ne...btex#hasPublisher	The Tenth Blue Danube Symposium on Heterocyclic Chemistry
https://schema.org/isbn	80-227-1938-2
http://localhost/t...ganizacniJednotka	22310

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